Regio- and stereo-specific synthesis of threo-3-amino-2-hydroxy-acids, novel amino-acids contained in aminopeptidase inhibitors of microbial origin
- 1 January 1980
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- Vol. 7 (7) , 1618-1621
- https://doi.org/10.1039/p19800001618
Abstract
threo-3-Amino-2-hydroxy-4-phenylbutanoic acid, a novel amino-acid contained in bestatin, an inhibitor of aminopeptidase B and leucine aminopeptidase, and threo-3-amino-2-hydroxy-5-methylhexanoic acid, a novel amino-acid contained in amastatin, an inhibitor of aminopeptidase A and leucine aminopeptidase, have been synthesized from cis- and trans-2-olefinic acids via regiospecific ring-opening of cis-2,3-epoxy-acids by ammonia. Direct hydroxyamination of the 2-olefinic acids, however, gave 2-amino-3-hydroxy-acids as the major products.This publication has 2 references indexed in Scilit:
- Structure and Chemical Synthesis of AmastatinAgricultural and Biological Chemistry, 1979
- Synthesis and structure-activity relations of bestatin analogs, inhibitors of aminopeptidase BJournal of Medicinal Chemistry, 1977