Dehydrooligopeptides. XVII. Practical Syntheses of All of the Diastereomers of N,N-Protected 2,3-Diaminobutanoic Acids from l- and d-Threonine Derivatives
- 1 May 1995
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 68 (5) , 1369-1377
- https://doi.org/10.1246/bcsj.68.1369
Abstract
Syntheses of all of the diastereomers of 2,3-diaminobutanoic acids, found in some peptide antibiotics and toxins, were accomplished. The four isomers were derived mainly through two pathways including SN2 inversions of the β-substituent of l- or d-threonine derivatives. The various protecting groups and effective nucleophiles for the SN2 inversion were examined.This publication has 8 references indexed in Scilit:
- Dehydrooligopeptides. XVI. Convenient Syntheses of Two Kinds of Antrimycins Av and Dv Containing Dehydrovaline ResiduesBulletin of the Chemical Society of Japan, 1994
- Enantioselective routes to protected syn- and anti-.beta.-phenylcysteinesThe Journal of Organic Chemistry, 1992
- Asymmetric hydrogenation catalyzed by rhodium complex with a new chiral bisphosphine derived from L-threonine.CHEMICAL & PHARMACEUTICAL BULLETIN, 1985
- Lavendomycin, a new antibiotic. I. Taxonomy, isolation and characterization.The Journal of Antibiotics, 1985
- Antrimycin, a new peptide antibiotic.The Journal of Antibiotics, 1981
- Structure of the peptide antibiotic amphomycinJournal of the American Chemical Society, 1973
- Synthesis of the Four Stereoisomeric Forms of α,β-Diaminobutyric Acid and Some Derivatives Suitable for Peptide SynthesisHoppe-Seyler´s Zeitschrift Für Physiologische Chemie, 1973
- ISOLATION AND IDENTIFICATION OF D-α-PIPECOLIC ACID, α[L],β-METHYLASPARTIC ACID AND α,β-DIAMINOBUTYRIC ACID FROM THE POLYPEPTIDE ANTIBIOTIC ASPARTOCINJournal of the American Chemical Society, 1960