Isolation and absolute configuration of SMTP-0, a simplest congener of the SMTP family nonlysine-analog plasminogen modulators.
SMTP-0, a new simple congener of the SMTP nonlysine-analog plasminogen modulators, was isolated from a culture of Stachybotrys microspora. Based on the physico-chemical data, SMTP-0 was shown to be an enantiomer of the antimicrobial compound stachybotrin B. The absolute configuration of SMTP-0 was determined by the modified Mosher method. The stereochemistry was further confirmed using an epimer of SMTP-0. Unlike most SMTPs with an amino acid side chain linked to the nitrogen atom of the lactam moiety, SMTP-0, which lacks the N-linked side chain, showed no plasminogen modulator activity.
Hasumi
Keiji
K
Department of Applied Biological Science, Tokyo Noko University, Tokyo, Japan. hasumi@cc.tuat.ac.jp
Hasegawa
Keiko
K
Kitano
Yoshikazu
Y
D000900:Anti-Bacterial Agents / Q000096:biosynthesis* / Q000494:pharmacology; D001578:Benzopyrans / Q000494:pharmacology*; D006801:Humans; D008239:Lysine; D010960:Plasminogen Activators / Q000096:biosynthesis* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D011760:Pyrrolidinones / Q000494:pharmacology*; D013191:Stachybotrys; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D001578:Benzopyrans; D011760:Pyrrolidinones; C105379:SMTP 1; C524348:SMTP-0 compound; D010960:Plasminogen Activators; D008239:Lysine