Transformation of an irregularly bridged epidithiodiketopiperazine to trichodermamide A

Prapairat Seephonkai; Palangpon Kongsaeree; Samran Prabpai; Masahiko Isaka; Yodhathai Thebtaranonth

doi:10.1021/ol061046l

Transformation of an irregularly bridged epidithiodiketopiperazine to trichodermamide A

Org Lett. 2006 Jul 6;8(14):3073-5. doi: 10.1021/ol061046l.

Authors

Prapairat Seephonkai¹, Palangpon Kongsaeree, Samran Prabpai, Masahiko Isaka, Yodhathai Thebtaranonth

Affiliation

¹ Department of Chemistry, Faculty of Science, Mahidol University, Bangkok, Thailand.

PMID: 16805555
DOI: 10.1021/ol061046l

Abstract

[reaction: see text] An unusually bridged epidithiodiketopiperazine, pretrichodermamide A (3), was isolated from the fungus Trichoderma sp. BCC 5926. During the extensive effort to crystallize 3 for X-ray crystallographic analysis, conversion of this compound to trichodermamide A with coproduction of S(8) occurred.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antitubercular Agents / chemistry
Antitubercular Agents / isolation & purification*
Antitubercular Agents / pharmacology
Crystallography, X-Ray
Dipeptides / chemistry
Dipeptides / isolation & purification*
Dipeptides / pharmacology
Molecular Conformation
Molecular Structure
Mycobacterium tuberculosis / drug effects*
Piperazines / chemistry*
Piperazines / isolation & purification*
Trichoderma / chemistry*

Substances

Antitubercular Agents
Dipeptides
Piperazines
pretrichodermamide A
trichodermamide A
gliovirin