A Convenient Synthesis of Methyl 2-[2-(1-Amino)ethenyl-bithiazolyl] thiazoline-4-carboxylate, an Important Skeleton of Cyclothiazomycin

doi:10.1246/CL.1995.45

Paper

A Convenient Synthesis of Methyl 2-[2-(1-Amino)ethenyl-bithiazolyl] thiazoline-4-carboxylate, an Important Skeleton of Cyclothiazomycin

Published 1995 · C. Shin, A. Ito, K. Okumura

Chemistry Letters

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10

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Abstract

The convenient syntheses of a few methyl 2-(1-amino)alkenyl thiazoline-4-carboxylates and methyl 2-[2-(1-amino)ethenyl-bithiazolyl] thiazoline-4-carboxylate have been accomplished. The latter is an important partial skeleton of macrobicyclic peptide antibiotic cyclothiazomycin.

Study Snapshot

This study successfully synthesized methyl 2-[2-(1-amino)ethenyl-bithiazolyl] thiazoline-4-carboxylate, an important skeleton of cyclothiazomycin, a macrobicyclic peptide antibiotic.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

A Convenient Synthesis of Methyl 2-[2-(1-Amino)ethenyl-bithiazolyl] thiazoline-4-carboxylate, an Important Skeleton of Cyclothiazomycin

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References

Convenient Syntheses of Thiazoles Incorporated with α-Dehydroamino Acid and Dehydropeptide Structures

This study successfully synthesized various thiazole -dehydroamino acids, thiazole valine ethyl ester, and their dehydrodiand tripeptides, which are important moieties and segments of micrococcin P1 and noshiheptide, macro

Cyclothiazomycin, a novel polythiazole-containing peptide with renin inhibitory activity. Taxonomy, fermentation, isolation and physico-chemical characterization.

Cyclothiazomycin, a novel renin inhibitor produced by Streptomyces sp. NR0516, shows inhibitory activity against human plasma renin with a 1.7 microM IC50.

The Chiral Synthesis of Thiazole Amino Acid Enantiomers

The modified Hantzsch reaction efficiently synthesizes optically pure thiazole amino acid derivatives, enabling the synthesis of novel chiral compounds like dolastatin 3.

Quinoline derivatives as degradation products from antibiotic thiopeptin B.

IR, NMR, and mass spectra confirm the structure of 4-acetyl-8-hydroxyquinaldic acid4>5) (I).

Citations

Visible-light-mediated decarboxylative benzoyloxylation of β-hydroxy amino acids and its application to synthesis of functional 1,2-amino alcohol derivatives

This novel method for decarboxylative benzoyloxylation of -hydroxy amino acids enables the synthesis of diverse chiral 1,2-amino alcohols with different aryl or alkyl groups, starting from serine or threonine derivatives.

Chiral thiazoline and thiazole building blocks for the synthesis of peptide-derived natural products.

Chiral thiazoline and thiazole building blocks are essential for the synthesis of peptide-derived natural products, aiding in structure confirmation, structure-activity relationship studies, and industrial production.

Synthetic studies on thiostrepton family of peptide antibiotics: synthesis of the dihydroquinoline portion of thiostrepton, the siomycins, and the thiopeptins

The one-pot olefination via the Matsumura-Boekelheide rearrangement and stereoselective addition reaction successfully synthesized the dihydroquinoline portion of thiostrepton, siomycins, and thiopeptins, members of the thi

Synthetic studies on thiostrepton family of peptide antibiotics: synthesis of the cyclic core portion containing the dehydropiperidine, dihydroquinoline, l-valine, and masked dehydroalanine segments

The cyclic core portion of the thiostrepton family of peptide antibiotics was synthesized by coupling four segments and cyclizing at the amide bond between dehydropiperidine and masked dehydroalanine segments.

Synthetic studies on thiostrepton family of peptide antibiotics: synthesis of the pentapeptide segment containing dihydroxyisoleucine, thiazoline and dehydroamino acid

The study successfully synthesized a pentapeptide segment of thiostrepton family antibiotics, showcasing advanced techniques like β-lactone opening and oxidative syn-elimination.