Transformation of the marine natural product cyclotheonamide A by aqueous base. X-ray analysis of a novel ligand complexed with human α-thrombin

Treatment of the macrocyclic pentapeptide cyclotheonamide A ( 1) with aqueous sodium carbonate or triethylamine at 23°C generated two isomeric products. X-ray analysis of a complex with α-thrombin indicates a ring-opened pentapeptide, 2, from cleavage at the α-keto amide bond. However, given the MS...

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Bibliographic Details
Published in:Tetrahedron letters 1996-05, Vol.37 (21), p.3667-3670
Main Authors: Maryanoff, Bruce E, Zhang, Han-Cheng, Greco, Michael N, Zhang, Erli, Vanderhoff-Hanaver, Peggy, Tulinsky, Alexander
Format: Article
Language:English
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Summary:Treatment of the macrocyclic pentapeptide cyclotheonamide A ( 1) with aqueous sodium carbonate or triethylamine at 23°C generated two isomeric products. X-ray analysis of a complex with α-thrombin indicates a ring-opened pentapeptide, 2, from cleavage at the α-keto amide bond. However, given the MS data for 3 and a model study in which 4 provides 5, structure 3 is suggested for the product from base treatment of 1. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/0040-4039(96)00658-2