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MELVILLE LAWRENCE WOLFROM April 2,1900-June 20,1969 BY DEREK HORTON AND W. Z. HASSID MELVILLE WOLFROM was born in Bellevue, Ohio, on April 2, 1900. He was the youngest of nine children in the family of Frederick Wolfrom and Maria Louisa (Sutter) Wolfrom. Originally, Melville's father's name was Friedrich Wolfrum, but some time before his marriage he anglicized it to Frederick Wolfrom. Melville's grandfather, Johann Lorenz Wolfrum, brought his family to America from the Sudeten German border town of Asch (now in Czechoslovakia) in 1854 and settled in a log cabin near Weaver's Corners, Sherman Township, Huron County, Ohio. Friedrich Wolfrum attended the county schools and worked from an early age to help support the family. For many years he was in the dry goods business in a store in nearby Bellevue, Ohio, and later worked as secretary-treasurer of a local tele- phone company that was the forerunner of the Ohio Northern Telephone Company. He died when Melville was only seven years old; as a result, from an early age Melville was instilled with the need for self-reliance. When still quite young, he worked on odd jobs, especially during the summers. His mother had a great respect for cultural pursuits, such as music and good literature, and stimulated in him an interest in serious reading. Melville was brought up in a very strict orthodox Lutheran tradition; and, although in later years he did not 487

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488 BIOGRAPHICAL MEMOIRS adhere to this strict religious background, he consistently ad- vocated some type of formal religious training for his children during their formative years. During his early teens, Melville became involved in a small manufacturing business maintained in the family home. His three oldest brothers bought the patent on a type of horse harness snap that was used successfully by several fire depart- ments. After school each day, on Saturdays and holidays, and throughout the summer vacations, Melville worked on the pro- duction of these harness snaps and was paid ten to fifteen cents an hour for his labor. During this time, he often tried to im- prove the devices and, as a result of this experience, determined to become a college graduate engineer with a view to a career in manufacturing. Melville attended Bellevue High School and graduated second in the class of 1917. Stimulating teachers helped him develop an early interest in nature study, fine arts, mathematics, and German. His first encounter with science was in high school, where he learned physical geography and botany from a Mr. S. A. Kurtz. Later, he was much influenced by Mr. W. A. Hammond, with whom he studied chemistry and, later, physics. Hammond's influence was primarily responsible for Melville's decision to become a chemist, or, more specifically, a chemical engineer; the more "practical" aspect of the latter field was appealing as a result of his earlier experience in the workshop. Being without family financial support, Melville was un- able to enter college upon graduation from high school. In- stead, he obtained a position with the National Carbon Com- pany, a firm manufacturing wet and dry batteries in the nearby town of Fremont. There, in the works laboratory, he tested the quality of the daily products. Within six months he was placed, at the age of seventeen, in charge of the laboratory, with about six persons under him. Here he conducted his first research

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MELVILLE LAWRENCE WOLFROM 489 project, an evaluation of the physical properties of carbon dry- cell electrodes as a function of the conditions used in baking the electrodes. During the winter, he took an evening course in qualitative inorganic analysis, given at the plant. Early the following summer, he resigned his post to go to Cleveland, with the idea of entering Western Reserve University in the autumn and earning his board by waiting on tables. He worked during the summer at a boarding house and also at a variety of jobs in factories and laboratories in Cleveland that were busy at that time with war production. That autumn, the government estab- lished the Students' Army Training Corps, and Melville entered the naval unit at Western Reserve. The prescribed course of study included physics, but no chemistry. The courses were un- inspiring, much disorganization resulted from the influenza epidemic, and he disliked the barracks life and the snobbish fraternity system of the school. When the armistice came in November 1918, he returned home to Bellevue feeling frus- trated. After working for a brief period as an advertising representa- tive for a trade paper, in the autumn of 1919 he entered Washington Square College of New York University. The col- lege unit was new and was not functioning well; no chemistry was offered. Again, he gave up his studies and returned to Bellevue, where he felt regarded as a disgrace and misfit. The following year he worked at odd jobs, as a laborer and then as a bookkeeper. Finally, in the autumn of 1920 he entered The Ohio State University in Columbus and embarked on a course in chemical engineering, an endeavor that at last held his attention and interest and that he enjoyed greatly. For his board, he worked at boarding houses, restaurants, and cafe- teriasas waiter, counter man, and dishwasher; he preferred the last kind of work. In general, he always preferred working with material things rather than with people; this preference was

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490 B I O G R A P H I C A L M E M O I R S evident throughout his life, although he had an unexpectedly perceptive insight into the character of those people he got to know. Young Wolfrom's first encounter with the chemistry of carbohydrates came at the end of his sophomore year, when Professor C. W. Foulk recommended him for a post as student research assistant to Professor William Lloyd Evans of the De- partment of Chemistry. The stipend was $250 per year, and Wolfrom put in all of his extra time on the work. During his junior year, he carried out quantitative oxidations of maltose with permanganate at various temperatures and concentrations of alkali. In his senior year, he attempted unsuccessfully to synthesize amino acid esters of glycerol. None of this work was published, but it was a good introduction to chemical research. Professor Evans, a student of J. U. Nef's, was very research- minded and inspirational. Wolfrom continued his work with Professor Evans and received the A.B. degree (cum laude) in 1924. The influence of Professor Evans and the other inspira- tional teachers of his undergraduate days was to endure through- out his career; the broad interdisciplinary approach that he took to research and the insistence upon careful observation, clear expression, and historical accuracy can all be traced to the early roots of his undergraduate training. During every summer of his college career, Wolfrom worked at Gypsum, Ohio, with his high school chemistry teacher, W. A. Hammond, who was plant chemist for that installation of the United States Gypsum Company. Melville's well-to-do uncle, Frank A. Knapp, impressed by his nephew's progress, offered to loan him the funds to complete his college work, but Mel- ville's mother sternly forbade him _~___ _ , 1 1 . r. . ~ ~ to take advantage of this oIrer, as 1l ala not nt into ner scheme of Spartan training for him. Following graduation from The Ohio State University, Wol- from moved to Northwestern University, in Evanston, Illinois, to

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MELVILLE LAWRENCE WOLFROM 491 carry out his graduate work under Professor W. Lee Lewis, a student of Nef's. He began research immediately and worked on it night and day, completing the M.Sc. degree in 1925 and the Ph.D. in 1927. His problem was to provide experimental evidence for the enediol theory advanced by Wohl and Neuberg to explain the Lobry de Bruyn-Alberda van Ekenstein inter- conversion of sugars in alkaline media. He observed that 2,3,4,6-tetra-0-methyl-D-glucose could be equilibrated with the D-manno epimer in aqueous alkali and that there was no loss of the 2-0-methyl group and no formation of keto sugars. The result pointed to an enediol intermediate common to the two methylated sugars and showed that the mechanism of enol for- mation was not one of selective hydration and dehydration, as had been suggested by Nef, but rather was consistent with a simple keto-enol tautomerism. This work, published with Lewis in 1928, was the first in what was to become Wolfrom's remarkably prolific output of research Caners on the sugars ex- tending over more than four decades and numbering more than five hundred individual reports. He had a phenomenal memory for detail from his early work; forty years after his paper with Lewis was published, he could still describe it in 1 1 OCR for page 486
492 BIOGRAPHICAL MEMOIRS sity, where she met her future husband. Throughout their married life, she continued to be involved in music teaching and in musical activities in the community and was ever a sympa- thetic and stimulating helpmate to her husband. After receiving his Ph.D. degree from Northwestern, Wolfrom was awarded a National Research Council Fellowship that enabled him to undertake a period of postdoctoral study with some of the leading investigators in his field of interest. First, he went to study with Claude S. Hudson, then at the National Bureau of Standards, in Washington, D.C., and the undisputed leader on the American scene in research on carbo- hydrates. Hudson, a student of Van' t Hoff's, had a strong background in physical chemistry; and his individualistic phi- losophy of research impressed Wolfrom greatly: his continuity of purpose, his exacting standards in experimental work, and his conservatism in theorizing until a thorough basis of facts had been recorded. All of these attributes, together with Hudson's concise and lucid style of writing, were to serve as models to Wolfrom throughout his career. It is doubtful that two such strong personalities could have long coexisted in the same in- stitution, but Wolfrom ever after regarded Hudson as an inspir- ing teacher and colleague, to whom he owed a great deal. Years later, they were to be closely associated in editorial and nomenclatural work, and they much enjoyed each other's com- pany. After a few months in Washington, Wolfrom moved in September 1927 to New York City in order to work in the laboratory of P. A. Levene at the Rockefeller Institute for Medical Research. Levene, the outstanding master on the North American continent in the young discipline of biochem- istry, was an ardent genius with a remarkable capacity for hard work and an urbane and cosmopolitan personality; he had a warm interest in all of those who worked with him. In his

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MELVILLE LAWRENCE WOLFROM 493 contact with Levene, Wolfrom was able to assimilate at first hand some of the valuable aspects of the European traditions in science that Levene was able to convey to his co-workers at the Rockefeller Institute, and he was simultaneously exposed to the enormous challenge to the structural chemist offered by the seemingly hopeless slimes and mucins that were components of animal tissues. Levene had realized that more needed to be known about the structures of the simple sugars, especially the linkage positions in the disaccharides and the ring size in cyclic monosaccharide derivatives, before he could ever hope to achieve his goal of structural elucidation in the nucleic acids. Wolfrom worked with him on these aspects, and, within a few months, a paper resulted on the Wohl degradation of cello- biose and its use in determining interglycosidic linkage-position. In quick succession thereafter were published two more papers on the ring structures of methyl D-lyxosides. In the summer of 1928 Wolfrom returned to The Ohio State University to finish up his two-year fellowship. There he worked independently on the synthesis of stable derivatives of the acyclic forms of the sugars, as such acyclic intermediates had been so often proposed as transient species in reactions of the sugars. By re- moving the thioacetal groups from the pentaacetate of D-glucose diethyl dithioacetal, he was able to obtain and characterize the acetate of the free aldehyde form of D-glucose; similar work in the D-galactose series followed later. In the autumn of 1929, Wolfrom was appointed Instructor in Chemistry at The Ohio State University and one year later was raised to the rank of Assistant Professor. He remained on the faculty of the Department of Chemistry at Ohio State for the whole of his career, becoming Associate Professor in 1936 and Professor in 1940. In 1939 he was awarded a fellowship by the John Simon Guggenheim Memorial Foundation; and, in February of that year, he traveled to Switzerland to work in

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494 BIOGRAPHICAL MEMOIRS the laboratory of Professor P. Karrer of the University of Zurich but returned to the United States at the outbreak of hostilities in Western Europe. With the aid of the successive generations of students who came to carry out their graduate research under his direction, Professor Wolfrom was able to launch a wide-ranging program of research, with problems of structure and reactivity in the carbohydrate field constituting the principal theme. The pro- cedures used for obtaining acetylated aldehydo-D-glucose were systematically extended through the sugar series, and new types of aldose derivatives containing substituents on the hydrated carbonyl gTOUp were obtained; these showed the predictable behavior in being isolable in two isomeric forms, epimeric at C-1. The new well-established fact that acyclic structures can exist as reactive sugar-intermediates, sometimes having con- siderable stability, rests largely on his pioneering work. His first Ph.D. student, Alva Thompson, showed that the acetylated r ~ . ~ ~ ~ oxime of D-glucose undergoes conversion from a cyclic to an acyclic form during the Wohl degradation, and for this work Thompson received the Ph.D. degree in 1931. Professor Wolfrom often appeared rather formidable and awesome to the new graduate student, even though he was physically only of medium height and build. He expected of his colleagues the standards of work that he set for himself. It was often difficult for lesser people to live up to his standards. His own experimental research was always done with precision, and he was proud to show that the samples he had prepared ~ ~ or I' I' ~ I. n~mse~r In one tn~rt~es were unctecomposect several decades later and that their purity was unimpeachable, even by the chroma- tographic techniques later developed. He expected that all melting points and optical rotations recorded by his students should be as authoritative as his own experimental values. Not every student or colleague who came into contact with Wolfrom could accept his uncompromising standards. Professor

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MELVILLE LAWRENCE WOLFROM 495 Wolfrom chose to expend his energies in those areas where the problems could be clearly defi-necl; and, once he had decided what was the right course, he held steadfast to that position, regardless of outside pressures. He tended to avoid becoming involved in situations where negotiations and compromises had to be made, or where the issues could not be stated in precise terms. A hard taskmaster, Wolfrom earned the greater respect of many of his students after they had completed their work with him. Despite his rather retiring and diffident manner toward groups of people not known to him, and despite the apparent gruffness and terseness that so often characterized his day-to-day contacts with his co-workers, he actually took a deep interest in the welfare of every colleague and student who had a genuine interest in, and aptitude for, science. He went to considerable lengths to help each of his students become established in a suitable post after graduation and kept in touch with a sur- prisingly large proportion of them long after their departure. He had a deep insight into human personality and found-it intriguing to delve into the background and motivations of each of the persons with whom he worked. This interest is reflected in the number of biographical memoirs that he chose to write, especially of his early mentors; these were done with char- acteristic thoroughness and show his perceptive qualities in understanding human nature. Although he never regarded lightly any of the work he undertook, Wolfrom had a very strong sense of humor, not always recognized by those who did not know him well. He had an endless store of anecdotes concerning the personalities of science, based on his own contacts with other scientists and on his wide reading of the history of science; the humor of his dry remarks would once in a while be betrayed by a fleeting smile. This side of his personality was most in evidence when he was with small groups of people he knew well and with small classes -

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496 BIOGRAPHICAL MEMOIRS of advanced students who were perceptive enough to appreciate the subtleties of his comments. His approach to teaching was always based on a solid, his- torical foundation that traced the development of science through the major milestones of factual knowledge, rather than through rationalizations and correlations that involved extrapo- . . ~ . . . ~ . at~on ot existing Information. At the graduate level, where he supervised almost a hundred Ph.D. students and numerous M.S. candidates, Professor Wolfrom made his major educational contribution. With these students he was able to pursue research on several broad fronts in the field of the carbohydrates. (A list of Wolfrom's published articles and the participating co-workers is given at the end of this memoir.) In the early days, most of the research students were employed as part-time teaching assistants in chemistry at Ohio State. Later, and especially after World War II, outside funding through grants and contracts from government and industry became available, and Wolfrom was able to expand his research program further. The research group was enriched by a regular succession of postdoctoral associates who came from other institutions for one or two years of experience in Professor Wolfrom's laboratory. The group became very cosmopolitan, always containing members from Europe and Asia, and Wolfrom particularly appreciated the new ideas and techniques brought in by these colleagues who had received their doctoral training in other laboratories. Throughout his career, Wolfrom's early theme of research on the acyclic forms of the sugars continued; in fact, one of his posthumous articles is a book chapter on the subject. Extending the route developed for aldehydo-D-glucose pentaacetate, he devised general methods for obtaining crystalline acetates of those sugars in which the carboyl group, aldehydic or ketonic, was present in the free form, uncombined with any hydroxyl group of the sugar chain; and the general chemistry of the

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542 BIOGRAPHICAL MEMOIRS "Osage Orange Pigments. XVI. The Structure of Alvaxanthone," ilk. L. Wolfrom, F. Komitsky, fir., and P. M. Mundell, T. Org. Chem., 30., 1088-1091. "Isomerization of Tetra-O-acetyl- 1 -deoxy-D-arabino-hex- 1 -enopyra- nose," R. U. Lemieux, D. R. Lineback, M. L. Wolfrom, F. B. Moody, E. G. Wallace, and F. Komitsky, Jr., J. Org. Chem., 30', 1092-1096. "Halogen and Nucleoside Derivatives of Acyclic 2-Amino-2-deoxy-D- glucose. II," M. L. Wolfrom, H. G. Garg, and D. Horton, I. Org. Chem., 30' 1096-1098. "Nucleosides of D-Glucuronic Acid and of D-Glucofuranose and D- Galactofuranose," M. L. ~Nolfrom and P. McWain, [. Org. Chem., 30' 1099-1101. "Synthesis of D-lyxo-Hexulose (D-Tagatose ) and 1-Deoxy-D-lyxo-hexu- lose," M. L. Wolfrom and R. B. Bennett, T. Org. Chem., 30', 1284-1287. "2,6-Diamino-2,6-dideoxy-D-mannose Dihydrochloride," M. L. Wol- from, P. Chakravarty, and D. Horton, Chem. Commun., 143. "Extrusion Column Chromatography on Cellulose," M. L. Wol- from, D. H. Busch, Rosa M. de Lederkremer, Sharon C. Vergez, and l. R. Vercellotti, 7. Chromatogr., 18' 42-46. "The Anomeric 9-~2-Amino-2-deoxy-D-glucopyranosyl~adenines, M. L. Wolfrom, H. G. Garg, and D. Horton, 7. Org. Chem., 30 1556-1560. "Products from the Ortho Ester Form of Acetylated Maltose," M. L. Wolfrom and Rosa M. de Lederkremer, .1. Org. Chem., 30', 1560- 1563. "Two Forms of 2-0-~2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-,8- D-glucopyranosyl)-1,3-O-benzylideneglycerol," W. A. Szarek, M. L. Wolfrom, and H. Tomomatsu, Chem. Common., 326-32~7. "Amino Derivatives of Starches. 2,6-Diamino-2,6-dideoxy-D-mannose Dihydrochloride," M. L. Wolfrom, P. Chakravarty, and D. Hor- ton, [. Org. Chem., 30', 2728-2731. "Acyclic Sugar Nucleoside Analogs. III," M. L. Wolfrom, W. van Bebenburg, R. Pagnucco, and P. Unchain, I. Org. Chem., 30' 2732-2735. "Ethyl 3,4,6-Tri-O-acetyl-2-amino-2-deoxy- 1 -thio-~-D-glucopyrano- side," M. L. Wolfrom, W. A. Cramp, and D. Horton, ]. Org. Chem., 30., 3056-3058.

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i~ELVILLE LAWRENCE WOLFROM 543 "Benzylsulfonyl as N-Blocking Group in Amino Sugar Nucleoside Synthesis," M. L. Wolfrom and R. Wurmb, J. Org. Chem., 30, 3058-3061. "Osage Orange Pigments. XVII. 1,3,6,7-Tetrahydroxyxanthone from the Heartwood," M. L. Wolfrom and H. B. Bhat, Phytochemis- try, 4, 765-768. "Synthesis of Diamino Sugars from 1,2-Diamino-1,2-dideoxyalditols. 4,5-Diacetamido-4,5-dideoxy-~-xylose," M. L. Wolfrom, l. L. Minor, and W. A. Szarek, Carbohyd. Res., 1, 156-163. "Amino Derivatives of Starches. Derivatives of 3,6-Diamino-3,6-di- deoxy-D-altrose," M. L. Wolfrom, Yen-Lung Hung, and Derek Horton, J. Org. Chem., 30, 3394-3400. "Isomaltose Synthesis Utilizing 2-Sulfonate Derivatives of D-Glu- cose," M. L. Wolfrom, K. Igarashi, and K. Koizumi, [. Org. Chem., 30, 3841-3844. "Chemical Evidence for the Structure of Starch," M. L. Wolfrom and H. E1 Khadem, in "Starch: Chemistry and Technology. Vol. I. Fundamental Aspects," R. L. Whistler and E. F. Paschall, Eds., Academic Press, Inc., New York, pp. 251-278. "Carbohydrates of the Coffee Bean. IV. An Arabinogalactan," M. L. Wolfrom and D. L. Patin, 7. Org. Chem., 30, 4060-4063. Advances in Carbohydrate Chemistry, Vol. 20, edited by M. L. Wolfrom and R. S. Tipson, Academic Press, Inc., New York. "Stereoisomere Formen des Athyl-hemiacetals van ald ehyd o-D- Galaktosepentaacetat," M. L. Wolfrom and William H. Decker, Liebigs Ann. Chem., 690, 163-165. Methods in Carbohydrate Chemistry, Vol. V, "General Polysac- charides," Roy L. Whistler, Ed., 1 chapter by M. L. Wolfrom and N. E. Franks, Academic Press, New York, pp. 276-279. 1966 "A Chemical Synthesis of Panose," M. L. Wolfrom and K. Koizumi, Chem. Commun., 2. "Trifluoroacetyl as [V-Blocking Group in Amino-sugar Nucleoside Synthesis," M. L. Wolfrom and H. B. Bhat, Chem. Commun., 146. "2-Amino-2-deoxy-D-xylose and 2-Amino-2-deoxy-D-ribose and Their 1-Thioglycofuranosides," M. L. Wolfrom and M. W. Winkley, J. Org. Chem., 31, 1169-1173.

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O44 BIOGRAPHICAL MEMOIRS "Configuration of the Glycosidic Linkage of 2-Amino-2-deoxy-wglu- copyranose to D-Glucuronic Acid in Heparin," M. L. Wolfrom, H. Tomomatsu, and W. A. Szarek, I. Org. Chem., 31' 1173-1178. "Quantitative Thin-layer Chromatography of Sugars on Micro- crystalline Cellulose," M. L. Wolfrom, Rosa M. de Lederkremer, and Gerhart Schwab, I. Chromatogr., 22', 474-476. "Starch Acetals. O-Tetrahydropyran-2-yl and O-(l-Alkoxyethyl) De- rivatives of Starch," M. L. Wolfrom, S. S. Bhattacharjee, and G. G. Parekh, Die Starke, 18,131-135. "Amino Derivatives of Starches. Sulfonation Studies on Methyl 3,6- Anhydro-~-D-glucopyranoside and Related Derivatives," M. L. Wolfrom, Yen-Lung Hung, P. Chakravarty, G. U. Yuen, and D. Horton, ]. Org. Chem., 3192227-2232. "Amino Derivatives of Starches. 2-Amino-3,6-anhydro-2-deoxy-D- mannose," M. L. Wolfrom, P. Chakravarty, and D. Horton, I. Org. Chem., 31, 2502-2504. "Two-Dimensional Thin-layer Chromatography of Amino Acids on Microcrystalline Cellulose," D. Horton, A. Tanimura, and M. L. Wolfrom, ]. Chromatogr., 23, 309-312. "Anomeric Nucleosides of the Furanose Forms of 2-Amino-2-deoxy- D-glucose and 2-Amino-2-deoxy-D-ribose," hi. L. Wolfrom and M. W. Winkley, Chem. Common., 533-534. "Alkaline Hypochlorite Oxidation of Methyl ,0-Cellol~ioside," M. L. Wolfrom and Rosa PI. de Lederkremer, Carbohyd. Res., 2', 426- 438. "Synthesis of a D-Glucofuranosyl Nucleoside Derivative Through an Oxazoline," M. L. Wolfrom and M. W. Winkley, J. Org. Chem., 31' 3711-3713. Advances in Carbohydrate Chemistry, Vol. 21, edited by M. L. Wol- from and R. S. Tipson, Academic Press, Inc., New York. 1967 "Bis~phenoxy~phosphinyl as N-Blocking Group in Amino Sugar Nucleoside Synthesis," M. L. Wolfrom, P. J. Conigliaro, and E. ]. Soltes, I. Org. Chem., 32, 653-655. "A Chemical Synthesis of Panose and an Isomeric Trisaccharide," M. L. Wolfrom and K. Koizumi, J. Org. Chem., 32' 656-660. "On Sulphate Placement in Heparin," M. L. Wolfrom and P. Y. Wang, Chem. Commun., 241. "Osage Orange Pigments. XVIII. Synthesis of Osaj axanthone, ,,

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MELVILLE LAWRENCE WOLFROM 545 M. L. Wolfrom, E. W. Koos, and H. B. Bhat, 7. Org. Chem., 32, 1058-1060. "Carbohydrate Nomenclature," M. L. Wolfrom, 7. Chem. Doc., 7, 78-81. "Substituted Arylazoethylenes from Aldose Arylhydrazones," H. E1 Khadem, M. L. Wolfrom, Z. M. E1 Shafei, and S. E1 Ashry, Carbohyd. Res., 4, 225-229. "Trichloroacetyl and Trifluoracetyl as N-Blocking Groups in Nu- cleoside Synthesis with 2-Amino Sugars," M. L. Wolfrom and H. B. Bhat, J. Org. Chem., 32' 1821-1823. "Anomeric Purine Nucleosides of the Furanose Form of 2-Amino-2- deoxy-D-ribose, M. L. M7olfrom and M. W. Winkley, 7. Org. Chem., 32', 1823-1825. "Polysaccharides from Instant Coffee Powder," M. L. Wolfrom and L. E. Anderson, I. Agr. Food Chem., 15,, 685-687. "2,4-Dinitrophenyl as IV-Blocking Group in Pyrimidine Nucleoside Synthesis with 2-Amino Sugars," M. L. Wolfrom and H. B. Bhat, J. Org. Chem., 32., 2757-2759. "Amino Derivatives of Starches. Amination of 6-O-Tritylamylose," M. L. Wolfrom, H. Kato, M. I. Taha, A. Sato, G. U. Yuen, T. Kinoshita, and E. J. Soltes, 1 O,-g. Chem., 32', 3086-3089. "Novel Reaction of a Nitro Sugar with Methanol," M. L. Wolfrom, U. G. Nayak, and T. Radford, Science, 157', 538. "A Novel Reaction of a Nitro Sugar with Alcohols," M. L. Wolfrom, U. G. Nayak, and T. Radford, Proc. Nat. Acad. Sci. U.S., 58' 1848-1851. Advances in Carbohydrate Chemistry, Vol. 22, edited by M. L. Wol- from and R. S. Tipson, Academic Press, New York. 1968 "Amination of Amylose Oxidized with Dimethyl Sulphoxide-Acetic Anhydride," M. L. Wolfrom and P. Y. Wang, Chem. Commun., 113-114. "Reaction of Alkyl Vinyl Ethers with Methyl a-D-Glucopyranoside," M. L. Wolfrom, Anne Beattie, and Shyam S. Bhattacharjee, 7. Org. Chem., 33' 1067-1070. "~-Iduronic Acid in Purified Heparin," M. L. Wolfrom, S. Honda, and P. Y. Wang, Chem. Commun., 505-506. "Glycosides, Natural," M. L. Wolfrom, in "The Encyclopaedia Britannica," Chicago, Ill., pp. 501-502.

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546 BIOGRAPHICAL MEMOIRS "Pectin," M. L. Wolfrom, in "The Encyclopaedia Britannica," Chi- cago, Ill., p. 515. "Carbohydrates," M. L. Wolfrom, in "The Encyclopaedia Britan- nica," Chicago, Ill., pp. 863-868. Tables, George G. Maher and M. L. Wolfrom, in "Handbook of Biochemistry," Section D, Carbohydrates, H. A. Sober, Ed., The Chemical Rubber Co., Cleveland, Ohio, pp. D1-D80. "Reaction of 3,4-Dihydro-2H-pyran with Methyl ~x-D-Glucopyrano- side," M. L. Wolfrom, Anne Beattie, S. S. Bhattacharjee, and G. G. Parekh, .1. Org. Chem., 33, 3990-3991. "AnomericAdenineNucleosides of 2-Amino-2-deoxy-D-ribofuranose," M. L. Wolfrom, M. W. Winkley, and P. McWain, in "Synthetic Procedures in Nucleic Acid Chemistry," Vol. I, W. W. Zorbach and R. S. Tipson, Eds., John Wiley and Sons, Inc., New York, pp. 168-171. " 1 -(Adenin-9-yl)- 1 -deoxyl- 1-S-ethyl- 1 -thio-aldebydo-D-galactose Alde- hydrol," M. L. Wolfrom, P. McWain, and A. Thompson, in "Synthetic Procedures in Nucleic Acid Chemistry," Vol. I, W. W. Zorbach and R. S. Tipson, Eds., John Wiley and Sons, Inc., New York, pp. 219-223. "9-~-Acetamid~3,b,6-tri-O -acetyl-2-deoxy-D-glucosyl)-2,6-dichloro-9H- purine," M. L. Wolfrom, M. W. Winkley, and P. McWain, in "Synthetic Procedures in Nucleic Acid Chemistry," Vol. I, W. W. Zorbach and R. S. Tipson, Eds., John Wiley and Sons, Inc., Ned York, pp. 239-241. " 1 -~2-Amino-2-deoxy-,8-D-glucopyranosyl )thymine, " M. L. Wolfrom, H. B. Bhat, and P. McWain, in "Synthetic Procedures in Nucleic Acid Chemistry," Vol. I, W. W. Zorbach and R. S. Tipson, Eds., John Wiley and Sons, Inc., New York, pp. 323-326. "Anomeric 2-Amino-2-deoxy-D-glucofuranosyl Nucleosides of Ade- nine and 2-Amino-2-deoxy-,B-~glucopyranosyl Nucleosides of Thymine and 5-Methylcytosine," M. L. Wolfram and M. W. Winkley, ]. Org. Chem., 33, 4227-4231. A dvances in Carbohydrate Chemistry, Vol. 23, edited by M. L. Wolfrom and R. S. Tipson, Academic Press, Inc., New York. 1969 "Quantitative Analysis of Gentiobiose and Isomaltose in Admixture, and Its Application to the Characterization of Dextrins," M. L. Wolfrom and G. Schwab, Carbohyd. Res., 9', 407-413.

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MELVILLE LAWRENCE WOLFROM o47 "On the Amination of Amylose," M. L. Wolfrom, K. C. Gupta, K. K. De, A. K. Chatterjee, T. Kinoshita, and P. Y Wang, Die Starke, 21, 39~3. "Anomeric Forms of 9-62-Amino-2-deoxy-D-xylofuranosyl~adenine," M. L. Wolfrom, M. W. Winkley, and S. Inouye, Carbohyd. Res., 10', 97-103. "The Isolation of ~-Iduronic Acid from the Crystalline Barium Acid Salt of Heparin," M. L. Wolfrom, ~ Inn And P Y wane Carbohyd. Res., 10' 259-265. "Starch Acetals. Acid Sensitivity and Preferred Site of Reaction," M. L. Wolfrom and S. S. Bhattacharjee, Die Starke, 21',116-118. "Trifluoroacetyl as an N-Protective Group in the Synthesis of Purine Nucleosides of 2-Amino-2-deoxy Saccharides," M. L. Wolfrom and P. l. Conigliaro, Carbohyd. Res., 11' 63-76. "Reaction of Carbohydrates with Vinyl Ethers; A Differential Hy- drolysis," M. L. Wolfrom, S. S. Bhattacharjee, and Rosa M. de Lederkremer, Carbohyd. Res., 11' 148-150. "Gas-liquid Chromatography in the Study of the Maillard Brown- ing Reaction," M. L. Wolfrom and N. Kashimura, Carbohyd. Res., 11, 151-152. "On the Distribution of Sulfate in Heparin," NI. L. ~Tolfrom, P. Y. Wang, and S. Honda, Carbohyd. Res., 11', 179-185. "Reaction of Alkyl Vinyl Ethers with D-Galactose Diethyl Dithio- acetal," M. L. Wolfrom and G. G. Parekl~, Carbohyd. Res., 11, 547-~57. _, ~ At,, Advances in Carbohydrate Chemistry and Biochemistry, Vol. 24, edited by M. L. Wolfrom, R. S. Tipson, and D. Horton, Academic Press, Inc., New York. "Mono- and Oligo-saccl~arides," M. L. Wolfrom in "Symposium on Foods: Carbohydrates and Their Roles," H. W. Schultz, R. F. Cain, and R. W. Wrolstad, Eds., Avi Publishing Co., Inc., West- port, Conn., pp. 12-25. 1970 Amination of Amylose at the C-2 Position," M. L. Wolfrom and P. Y. Wang, Carbohyd. Res., 12, 109-114. 1971 "A Synthetic Heparinoid from Amylose," M. L. Wolfrom arid P. Y. Wang, Carbohyd. Res., 18', 23-37.

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548 BIOGRAPHICAL MEMOIRS "Halogen and Nucleoside Derivatives of Acyclic 2-Amino-2-deoxy- D-glucose. III," M. L. Wolfrom and P. l. Conigliaro, Carbohyd. Res., 20, 369-374. "Pyrimidine Nucleosides of 2-Amino-2-deoxy-D-galactose," M. L. Wolfrom, H. B. Bhat, and P. I. Conigliaro, Carbohyd. Res., 20' 375-381. `'Pyrimidine Nucleosides of the Furanose Form of 2-Amino-2-deoxy- D-glucose," M. L. Wolfrom, P. l. Conigliaro, and H. B. Bhat, Carbohyd. Res., 20, 383-390. "Pyrimidine Nucleosides of the Furanose Form of 2-Amino-2-deoxy- D-xylose," M. L. Wolfrom and P. J. Conigliaro, Carbohyd. Res., 20, 391-398. "Esters," M. L. Wolfrom and Walter A. Szarek, in "The Carbohy- drates," Vol. IA, W. Pigman and D. Horton, Eds., Academic Press, Inc., New York, pp. 217-238. "Halogen Derivatives," M. L. Wolfrom and W. A. Szarek, in "The Carbohydrates," Vol. IA, W. Pigman and D. Horton, Eds., Academic Press, Inc., New York, pp. 239-~51. "Acyclic Derivatives," M. L. Wolfrom, in "The Carbohydrates," Vol. IA, W. Pigman and D. Horton, Eds., Academic Press, Inc., New York, pp. 355-422. 1972 "Acyclic-Sugar Nucleoside Analogs. Thymine Derivatives from Acyclic D-Galactose and D-Glucose Precursors," M. L. Wolfrom, H. B. Bhat, P. McWain, and D. Horton, Carbohyd. Res., 239 289-295. "Acyclic-Sugar Nucleoside Analogs. 6-Mercaptopurine Nucleosides Having Acyclic D-Galactose and D-Glucose Chains," M. L. Wol- from, P. McWain, H. B. Bhat, and D. Horton, Carbohyd. Res., 23, 296-300. "Effect of Ionizing Radiation on the Browning Reaction of D-Glu case, D-Fructose, Sucrose, and Raw-cane Sugar," W. W. Binkley, M. E. Altenburg, and M. L. Wolfrom, Sugar J., 34, 25-28. 1974 "A New Method of Acetonation, Synthesis of 4,6-O-Isopropylidene- D-glucopyranose," M. L. Wolfrom, A. B. Diwadkar, l. Gelas, and D. Horton, Carbohyd. Res., 35, 87-96.

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MELVILLE LAWRENCE WOLFROM 549 "Reactions of 4,b,6-Tri-O-benzoyl-1,3-dideoxy-1-diazo-D-erythro-hexu- lose," M. L. Wolfrom, N. Kashimura, and D. Horton, Carbohyd. Res., 36', 21 1-213. "Detection of Willard Browning Reaction Products as Trimethyl- silyl Derivatives by Gas-Liquid Chromatography," M. L. Wol- from, N. Kashimura, and D. Horton, J. Agr. Food Chem., 22, 791-795. "Factors Affecting the Maillard Browning Reaction between Sugars and Amino Acids. Studies on the Nonenzymic Browning of De- hydrated Orange Juice," J. Agr. Food Chem., 22' 796-800. 1975 "Four Isomeric Ethyl 1-Thioglycosides from 2-Amino-2-deoxy-D- arabinose," M. L. Wolfrom and S. Inouye, Carbohyd. Res., 41, 1 17-134. "Synthesis and Spectral Properties of Cytosine Nucleosides of 2- Amino-2-deoxy-D-arabinose," M. L. Wolfrom and S. Inouye, Carbohyd. Res., 42' 307-14. "Synthesis of a Cytosine Nucleoside of 2-Amino-2-deoxy-,8-D-xylo- furanose," M. L. Wolfrom, S. Inouye, and P. l. Conigliaro, Carbohyd. Res., 42' 327-34.

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ACKNOWLEDGMENTS FOR THE PHOTOGRAPHS Photograph of Paul Rufus Burkholder courtesy of the University of Georgia Once of Public Relations Photograph of Arthur Louis Day by Kaiden Kazanjian Photograph of William Draper Harkins by \Ioffett Photograph of Vladimir Nikolaevich Ipatieff courtesy of Louis Schmerling Photograph of Herbert Spencer Jennings from a portrait by Frank B. A. Linton Photograph of Alfred Harrison Joy by R. Kourken Photograph of John Rodman Paul courtesy of Dorothy M. Horstmann Photograph of William Thomas Pecora U.S. Department of the Interior Geological Survey Photograph of tack Schultz courtesy of T homes F. Anderson Photograph of Stanley Smith Stevens lay Paul Koby, Cambridge, Mass. Photograph of John Torrence Tate University of Minnesota Laboratory

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