TRANSFORMATION OF THE MARINE NATURAL PRODUCT CYCLOTHEONAMIDE A BY AQUEOUS BASE, X-RAY-ANALYSIS OF A NOVEL LIGAND COMPLEXED WITH HUMAN ALPHA-THROMBIN

Authors
MARYANOFF BE ZHANG HC GRECO MN ZHANG E VANDERHOFFHANAVER P TULINSKY A
Citation
Be. Maryanoff et al., TRANSFORMATION OF THE MARINE NATURAL PRODUCT CYCLOTHEONAMIDE A BY AQUEOUS BASE, X-RAY-ANALYSIS OF A NOVEL LIGAND COMPLEXED WITH HUMAN ALPHA-THROMBIN, Tetrahedron letters, 37(21), 1996, pp. 3667-3670
Citations number
12
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
21
Year of publication
1996
Pages
3667 - 3670
Database
ISI
SICI code
0040-4039(1996)37:21<3667:TOTMNP>2.0.ZU;2-Q
Abstract
Treatment of the macrocyclic pentapeptide cyclotheonamide A (1) with a queous sodium carbonate or triethylamine at 23 degrees C generated two isomeric products. X-ray analysis of a complex with alpha-thrombin in dicates a ring-opened pentapeptide, 2, from cleavage at the alpha-keto amide bond. However, given the MS data for 3 and a model study in whi ch 4 provides 5, structure 3 is suggested for the product from base tr eatment of 1. Copyright (C) 1996 Elsevier Science Ltd.