The Structure and Biological Activities of Hypoglycin

Ropp, R. S. De; Meter, J. C. Van; Renzo, E.C. De; McKerns, Kenneth W.; Pidacks, C.; Bell, Paul H.; Ullman, Edwin F.; Safir, S. R.; Fanshawe, William J.; Davis, Selby B.

doi:10.1021/ja01537a069

Cited by 28 publications

(17 citation statements)

References 2 publications

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“…Gas-phase infrared and mass spectra of the Id -formic acid confirmed the manufacturer's declared isotopic purity. Thus the very intense C-H band of HCOOH at 2930 cm-l was absent in the infrared spectrum of DCOOH [12], and the relative intensities of the m/e = 46 (DCOO+), 45 (COOH+), and 29 (HCO+) in the 70-eV mass spectrum of DCOOH were in agreement with literature reports [13]. The concentration of the formic acids was determined by titration with a standardized NaOH solution.…”

Section: Methodssupporting

confidence: 86%

Anomalous kinetic hydrogen isotope effect in the oxidation of formate by bromine: Tunneling via an intermediate

Brusa¹,

Colussi²

1982

Int J of Chemical Kinetics

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Rates of oxidation of XCOO-(X = H, D) by Brz in acid aqueous media were measured between 274 and 332 K. The derived Arrhenius parameters for both reactions log k~( M -l However, it can be shown that either tunneling in a single step or a three-step, internal return mechanism can be ruled out as alternative models, since both require unreasonable kinetic parameters to fit the data. The simplest scheme accounting for the present observations involves tunneling in the decomposition of a charge transfer complex in equilibrium with the reactants.

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Section: Methodssupporting

confidence: 86%

Anomalous kinetic hydrogen isotope effect in the oxidation of formate by bromine: Tunneling via an intermediate

Brusa¹,

Colussi²

1982

Int J of Chemical Kinetics

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“…42 The γ,δ-unsaturated amino acids are also biologically active. Allylglycine (42), crotylglycine (43), and methallylglycine (44) were identified in 1948 as inhibitors of microbial growth. 43 Hypoglycin A (45), an amino acid with hypoglycemic properties, has the structure β-(1-methyl-2-methylenecycloprop-1yl)alanine.…”

Section: Unusual Amino Acids In Drugsmentioning

confidence: 99%

“…43 Hypoglycin A (45), an amino acid with hypoglycemic properties, has the structure β-(1-methyl-2-methylenecycloprop-1yl)alanine. 44 It was isolated from the unripe fruit of ackee (Blighia sapida) in 1954, as it was believed that fruit might be responsible for "vomiting sickness" in Jamaica, where the fruit is a common part of the diet. 45 Hypoglycin A inhibits enzymes responsible for glucose synthesis, causing a dramatic lowering of blood sugar levels.…”

Section: Unusual Amino Acids In Drugsmentioning

confidence: 99%

Unusual Amino Acids in Medicinal Chemistry

2016

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Unusual amino acids are fundamental building blocks of modern medicinal chemistry. The combination of readily functionalized amine and carboxyl groups attached to a chiral central core along with one or two potentially diverse side chains provides a unique three-dimensional structure with a high degree of functionality. This makes them invaluable as starting materials for syntheses of complex molecules, highly diverse elements for SAR campaigns, integral components of peptidomimetic drugs, and potential drugs on their own. This Perspective highlights the diversity of unnatural amino acid structures found in hit-to-lead and lead optimization campaigns and clinical stage and approved drugs, reflecting their increasingly important role in medicinal chemistry.

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“…Thus, a linkage of S to C-3 required that C-2 be joined to C-3' or C-4 to form a cyclopropane ring, since cephalosporin C contained only one C-methyl and therefore C-2 could not be a methyl carbon. The resulting structures could account for the formation of valine from cephalosporin C on hydrogenolysis since the cyclopropane ring in the amino acid hypoglycin was known to be cleaved by catalytic hydrogenation (Ellington, Hassall & Plimmer, 1958;De Ropp et al 1958;Renner, Johl & Stoll, 1958). However, neither of the structures could accommodate a double bond or account for degradation products with the properties of compounds 1 and 2.…”

Section: Hs-mentioning

confidence: 99%