Marvin Carmack

Indiana University Bloomington, Bloomington, Indiana, United States

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Publications (34)134.38 Total impact

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    ABSTRACT: ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
    ChemInform 09/2010; 26(38). DOI:10.1002/chin.199538282
  • Marvin Carmack, Ian W. Stapleton, Richard Y. Wen
    Organic Preparations and Procedures International 02/2009; 1(4):255-258. DOI:10.1080/00304946909458394 · 1.19 Impact Factor
  • Marvin Carmack
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    ABSTRACT: In the Transmissible Spongiform Encephalopathies (TSEs) it has been generally assumed that the normal prion proteins (PPr) occurring on neural cells have the same composition of amino acids and the same sequence as the pathological forms (PPrSc) but differ in the manner of folding. The mechanism(s) by which the conversion of PPr into PPrSc takes place remain unknown. This paper calls attention to some aspects of chirality inherent in the disulfide function and suggests the possibility that handedness in the disulfide bond of prions may transmit stereochemical information that can influence the manner of folding or refolding into pathogenic forms.
    Journal of Chemical Information and Computer Sciences 05/2004; 44(1):286-8. DOI:10.1021/ci020073x
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    ABSTRACT: Olfactorily mediated puberty acceleration in female mice (measured by an increase in uterine weight) has been observed since the 1960s without the active chemosignal being structurally identified. There are many controversies in the literature as to whether this male-originated pheromone is a volatile substance. We investigated the chemical nature of the urinary fractions that are responsible for the characteristic uterine weight increases. The active pheromone was identified as 5,5-dimethyl-2-ethyltetrahydrofuran-2-ol and/or its open-chain tautomer (6-hydroxy-6-methyl-3-heptanone). A series of cyclic vinyl ethers were isolated from chromatographically active fractions of the urine. Because these compounds did not accelerate puberty, we postulated that these ethers were degradation products of a lactol (5,5-dimethyl-2-ethyltetrahydrofuran-2-ol). The lactol was then detected directly in the mouse urine extract using a silylation agent. Synthetic 6-hydroxy-6-methyl-3-heptanone had strong biological activity, whereas its close structural analogs did not. The male house mouse excretes into its urine a large quantity of a volatile substance that has a unique lactol/hydroxyketone structure. This substance is capable of binding to the less volatile urinary constituents, such as proteins or peptides, and is active in puberty-acceleration bioassays. The controversies regarding the volatility of the puberty-accelerating pheromones can now be explained by considering a complex of volatile lactol/hydroxyketone and urinary proteins.
    Chemistry & Biology 07/1999; 6(6):377-83. DOI:10.1016/S1074-5521(99)80049-0 · 6.59 Impact Factor
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    ABSTRACT: Two male mouse pheromones, 3,4-dehydro-exo-brevicomin (DHB) and 2-sec-butyldihydrothiazole (SBT), are chiral molecules which were previously tested in their respective bioassays as racemic mixtures. The focus of this study has been to determine the absolute configuration of their natural forms and its relation to stereospecific biological action. DHB was established as the R,R-enantiomer possessing biological activity. Due to an extremely easy racemization of SBT under very mild conditions, enantioselectivity of its transmission and its action at the receptor site appear to be of secondary importance.
    Experientia 08/1995; 51(7):738-43. DOI:10.1007/BF01941272
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    ABSTRACT: The structure of a new C19 bitter-tasting quassinoid, polyandrol, isolated from the root bark of Castela polyandra, was established.
    Phytochemistry 05/1995; 38(6):1463-5. DOI:10.1016/0031-9422(94)00817-D · 3.35 Impact Factor
  • Marvin Carmack
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    ABSTRACT: Marvin Carmack was born in 1913 near Dana, Vermillion County, Indiana, U.S.A., and attended public schools there. He graduated from the University of Illinois in 1937 with A.B. Honors in Chemistry. During 1937–40 he earned the M.S. and Ph.D. degrees at the University of Michigan, working with Professor Werner E. Bachmann on the synthesis of substituted benzopyrene compounds as potential carcinogens. At Michigan he carried out his first experiments with the Willgerodt Reaction, which remained one continuing subject of his interest for the next fifty years-an interest that broadened to include many aspects of sulfur chemistry.A year of post-doctoral research with Professor Roger Adams at the University of Illinois dealt with the isolation and determination of structures of alkaloids of the Crotalaria and Senecio species. This research resulted in the revision of the structure of retronecine, the common subunit of most of these alkaloids.In 1941 he joined the Faculty of Chemistry in the Towne Scientific School of the University of Pennsylvania in Philadelphia. At the beginning of World War II he became the Official Investigator of a contract between the University of Pennsylvania and the National Defense Research Committee of the Office of Scientific Research and Development. Its mission was the study of military high explosives. Later, under the Committee on Medical Research, his group investigated potentially antimalarial compounds.After World War II, his academic program was divided between the isolation and structure determination of natural products and the study of sulfur chemistry. He served as consultant to several industries and the Los Alamos National Laboratory. He has been a member of many scientific societies.During the academic year 1949–50, a Guggenheim Foundation Fellowship took him to the Swiss Eidgenössische Technische Hochschule in Zürich, where he worked with Professor Vladimir Prelog on the chemistry of the Erythrina alkaloids. A satisfying outcome that resulted from this research was a new spiro structure for the central ring system of the Erythrina alkaloids.He attained the rank of Professor of Chemistry at the University of Pennsylvania in 1951. In 1953, he moved to Indiana University as Professor of Chemistry, teaching graduate and undergraduate courses in organic chemistry and continuing research in natural products and sulfur chemistry. In 1960, he married Joan M. Scully of LaGrange, Illinois, and with her spent most of 1960–61 in Melbourne, Australia, under a Fulbright Research Fellowship. He worked in the laboratory of natural products chemistry directed by Dr. J. R. Price of the Commonwealth Scientific and Industrial Organisation. At that time, Dr. Price was coordinating a large program involving collection and broad screening of many unique plant species of Australia and New Guinea for therapeutically useful compounds.Carmack formally retired in 1978, with the rank of Professor Emeritus of Chemistry, but continued to be active within the Department of Chemistry at Indiana University. He worked informally with the research group under Rudy Professor of Analytical Chemistry, Dr. Milos Novotny. In addition to Dr. Novotny's main program of developing new and highly sensitive techniques in analytical chemistry, his group was also concerned with the application of their new technologies to the solution of problems in biology and medicine, among them the identification of mammalian pheromones. Working with Dr. Wesley K. Whitten and other noted biologists, the group studied pheromones of the red fox, the mouse, the wolf, and other species, and published a number of papers on the pheromones that were identified. Carmack's association with the Novotny group was concerned with the organic chemistry involved in the identification, structure determination, synthesis, and stereochemistry of specific mammalian pheromones.Carmack has been active in community affairs, serving as Board Member and Treasurer of the Boys' Club of Bloomington and the Society of the Friends of Music of Indiana University. He is a member of the Board of the Bloomington Hospital Foundation, and the Hospital's Advisory Council. In 1993, Carmack received the Indiana University President's Medal and Citation for Excellence in Teaching and Research.
    Sulfur Reports 04/1995; 16(2):299-340. DOI:10.1080/01961779508048741
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    ABSTRACT: The most unusual feature of the Willgerodt-Kindler Reactions is the facile isomerization of the carbonyl function along a chain of unbranched methylene groups, or around a cycloaliphatic ring containing several connected methylene groups. We have demonstrated that the first step in the Kindler process is the formation of enamines by reaction of the carbonyl function with secondary aliphatic amines, followed by reaction of the enamine with certain sulfur-amine catalysts to form reactive heterocyclic sulfur intermediates that facilitate the elimination-readdition of the amines reversibly along the chain. It was shown that compounds of the type R2N-S-S-NR2 are effective catalysts but not compounds of the type R2N-S-NR2. Some cyclohexanone derivatives undergo aromatization, with anomalous results in certain cases.
    Journal of Heterocyclic Chemistry 09/1989; 26(5):1305 - 1318. DOI:10.1002/jhet.5570260517 · 0.87 Impact Factor
  • Marvin Carmack
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    ABSTRACT: The mechanisms involved in various stages of the Kindler Reaction are discussed, with particular attention especially to its most unusual feature: the movement of a carbonyl group from methylene carbon to methylene carbon in an unbranched alkyl chain, or around a cycloalkyl ring. The first step is the reversible formation of an enamine, which is attacked by a catalyst generated from sulfur and the amine solvent to form a highly reactive intermediate with a sulfur-containing heterocyclic ring. The natures of the catalytically active species and the reactive intermediates are proposed. Other steps involved in the Kindler Reaction are also discussed, as is the relationship of the Willgerodt Reaction to the Kindler Reaction.
    Journal of Heterocyclic Chemistry 09/1989; 26(5):1319 - 1323. DOI:10.1002/jhet.5570260518 · 0.87 Impact Factor
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    ABSTRACT: Mouse urine contains a great number of volatile constituents that may be used in chemical communication. Some of these volatiles, identified in this study by combined gas chromatography-mass spectrometry and gas chromatography-Fourier-transform infrared spectroscopy, appear unique to the mouse. Certain urinary volatiles exhibit strong dependence on the sex and endocrine status of the animals, as shown through castration, treatment with an antiandrogen, and hormone supplementation.
    Journal of Chemical Ecology 01/1986; 12(1):277-96. DOI:10.1007/BF01045611 · 2.24 Impact Factor
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    ABSTRACT: Investigations regarding the chemical composition of the volatiles in male mouse urine have recently enabled the structural elucidation of a hitherto unreported urinary component, 7-exo-ethyl-5-methyl-6,8-dioxabicyclo[3.2.1]-3-octene. This compound's uniqueness to mouse urine and its dependence on testosterone levels in the male suggest its probable role as a mouse pheromone or pheromone adjuvant.
    Experientia 03/1984; 40(2):217-9. DOI:10.1007/BF01963608
  • The Journal of Organic Chemistry 03/1984; 49(5). DOI:10.1021/jo00179a025 · 4.64 Impact Factor
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    ABSTRACT: A control aqueous solution containing alcohol and polyethylene glycol, and a test solution with the addition of a mixture of eight volatile synthetic compounds identified in red fox urine, Were alternately placed on man-made mounds of fresh snow during January and February, the foxes'' courtship season. The foxes preferentially marked those mounds treated with the test solution in the two experimental areas (P < 0.05="" and="">
    Journal of Chemical Ecology 12/1979; 6(1):49-55. DOI:10.1007/BF00987526 · 2.24 Impact Factor
  • The Journal of Organic Chemistry 11/1978; 43(24):4675-4676. DOI:10.1021/jo00418a038 · 4.64 Impact Factor
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    ABSTRACT: Four volatile chemical compounds have been identified as apparently unique constituents in urines of red foxes (both sexes) during the winter season when mating occurs. Quinaldine was found only in male fox urine. Several other compounds identified are found in other species also. Some or all of these compounds may function in olfactory communication in the red fox.
    Science 03/1978; 199(4330):796-8. DOI:10.1126/science.199.4330.796 · 31.48 Impact Factor
  • Andrew P. Komin, Marvin Carmack
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    ABSTRACT: The o-diamine, 3,4-diamino-1,2,5-thiadiazole (2), was synthesized from 3,4-dichloro-1,2,5-thiadiazole (3) hy three methods. Aqueous glyoxal cyclized 2 into [1,2,5]thiadiazolo[3,4–6]-pyrazine (14). 3,4-Dichloro-1,2,5-thiadiazole 1,1-dioxide (18) reaeted with 2 to give 1,3-dihydro-bis[1,2,5]thiadiazolo[3,4-b:3′,4′-e]pyrazine 2,2-dioxide (19). The reaction of 2 with selenium oxyehloride led to [1,2,5]selenadiazolo[3,4-c] [1,2,5]thiadiazole (12). Ring closure of 2,3-diaminoquinoxaline (4) with thionyl chloride or selenium oxychloride gave [1,2,5]thiadiazolo-[3,4-b]quinoxaline (21) and [1,2,5]selenadiazolo[3,4-b]quinoxaline (22), respectively. Sulfurous acid reduced 21 to the 4,9-dihydro derivative 23, which was reoxidized to 21 with chloranil. Aqueous hase hydrolyzed 21 to 4via the hydrated intermediate 24. Aqueous glyoxal cyclized 4 to the covalent hydrate of pyrazino[2,3-b]quinoxaline (26), 27, which was dehydrated to 26. Compound 26 underwent rapid addition of two alcohols in a process analogous to covalent hydration.
    Journal of Heterocyclic Chemistry 02/1976; 13(1):13 - 22. DOI:10.1002/jhet.5570130102 · 0.87 Impact Factor
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    ABSTRACT: Three extracts of the roots of the plant Lithospermum ruderale (lithosperm) were tested for their ability to inhibit in vivo the action of endogenous and exogenous gonadotropins and of thyrotropin when measured by the 32P uptake of testes and thyroid glands of white Leghorn cockerels. Preparation, BD 893-122, was a crude extract and inhibited both endogenous gonadotropins and thyrotropin in 10-day-old birds. This extract, in addition, produced a 81.5% in vivo inhibition of exogenous TSH in 1-day-old chicks. Fractionation of root extracts on a Sephadex G-50 column resulted in several distinctive polyphenolic fractions, one of which, fraction E, inhibited exogenous FSH and endogenous TSH in 11-day-old cockerels. The inhibition of 32P uptake by the testes demonstrated that 70.8% inhibition of FSH occurred. The E fraction also markedly inhibited endogenous TSH. Fractions from the Sephadex G-50 column were further fractionated on a Sephadex G-25 column and fraction F-3, which was composed of 85% salts of lithospermic acid, was tested in 11-day-old chicks for its inhibitory effect in vivo against exogenous LH and FSH. F-3 inhibited 90.7% of the LH action and 63.5% of the FSH action but it was observed that it did not inhibit endogenous TSH in this experiment. Fractionation on the Sephadex G-25 column appeared to have separated the antigonadotropic and the antithyrotropic activities of lithosperm. The evidence also indicates that LH action was inhibited to a greater degree than was that of FSH.There was no indication that body weights or gland weights were depressed by the lithosperm fractions. It is improbable that the inhibitory action of the lithosperm fractions can be explained on the basis of either toxic effects or of inanition.
    General and Comparative Endocrinology 02/1976; 28(1):24-32. DOI:10.1016/0016-6480(76)90134-9 · 2.67 Impact Factor
  • The Journal of Organic Chemistry 02/1976; 41(3). DOI:10.1021/jo00865a007 · 4.64 Impact Factor
  • Biochemical and Biophysical Research Communications 01/1976; 67(3):1234-41. · 2.28 Impact Factor
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    ABSTRACT: A polyphenolic fraction of the plant was injected into White Leghorn cockerels at various time intervals and the effect on testes and thyroids was measured by the uptake of 32P. The 32P uptake 8 hours after lithosperm2 injection was markedly depressed and 12 hours after administration was notably increased. It is suggested that the hypothalamic regulation of the testes and thyroids is altered by lithosperm interference of the hypothalamic feedback system and/or the binding of receptor sites in the two glands.
    Biochemical and Biophysical Research Communications 12/1975; 67(3):1234-1241. DOI:10.1016/0006-291X(75)90805-0 · 2.28 Impact Factor