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First Total Synthesis and Biological Potential of a Heptacyclopeptide of Plant Origin
Author(s) -
Dahiya Rajiv,
Singh Sunil
Publication year - 2016
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201600419
Subject(s) - chemistry , tetrapeptide , tripeptide , anthelmintic , stereochemistry , peptide , antifungal , glycine , biological activity , cyclic peptide , combinatorial chemistry , amino acid , in vitro , biochemistry , microbiology and biotechnology , biology , ecology
Synthesis of a natural glycine‐rich heptacyclopeptide ‐ mahafacyclin A ( 7 ) was accomplished by solution‐phase technique of peptide synthesis via coupling of tetrapeptide unit Boc‐ L ‐Thr‐ L ‐Ile‐ L ‐Leu‐Gly‐OH with tripeptide unit L ‐Val‐ L ‐Phe‐Gly‐OMe followed by cyclization of linear heptapeptide fragment. Structure of the newly synthesized cyclopolypeptide was confirmed by means of chemical, spectroscopic analyses and subjected to antibacterial, antifungal and anthelmintic activity studies. Bioactivity results showed potent antifungal and anthelmintic activities of the synthesized peptide against dermatophytes T. mentagrophytes , M. audouinii and earthworm species M. konkanensis , P. corethruses and E. eugeniea .