Use of BOP-Cl in the presence of Boc-amino monothioacids for the thioacylation of imino acid residues

BOP-Cl was found to be an efficient coupling reagent for the introduction of thiopeptide bonds on imino acid residues (Pro, Sar). Boc-amino monothioacids were coupled at moderate temperature (0 degree C-RT) with fair yields and with retained optical purity. The mechanism of the coupling reaction is...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 1996-12, Vol.4 (12), p.2201-2209
Main Authors: Le, H T, Gallard, J F, Mayer, M, Guittet, E, Michelot, R
Format: Article
Language:English
Subjects:
Amino Acids - chemistry
Cross-Linking Reagents
Imines - chemistry
Leucine - chemistry
Models, Chemical
Organophosphorus Compounds - chemistry
Oxazoles - chemistry
Phosphorus - chemistry
Piperidines - chemistry
Proline - chemistry
Sulfhydryl Compounds - chemistry
Thioamides - chemistry
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Summary:BOP-Cl was found to be an efficient coupling reagent for the introduction of thiopeptide bonds on imino acid residues (Pro, Sar). Boc-amino monothioacids were coupled at moderate temperature (0 degree C-RT) with fair yields and with retained optical purity. The mechanism of the coupling reaction is discussed.
ISSN:0968-0896