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 discussed.
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Natural Products Chemistry Institute, C.N.R.S., Gif sur Yvette, France.
Gallard
J F
JF
Mayer
M
M
Guittet
E
E
Michelot
R
R
D000596:Amino Acids / Q000737:chemistry*; D003432:Cross-Linking Reagents; D007097:Imines / Q000737:chemistry*; D007930:Leucine / Q000737:chemistry; D008956:Models, Chemical; D009943:Organophosphorus Compounds / Q000737:chemistry*; D010080:Oxazoles / Q000737:chemistry*; D010758:Phosphorus / Q000737:chemistry; D010880:Piperidines / Q000737:chemistry; D011392:Proline / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000737:chemistry; D013854:Thioamides / Q000737:chemistry*
D000596:Amino Acids; D003432:Cross-Linking Reagents; D007097:Imines; D009943:Organophosphorus Compounds; D010080:Oxazoles; D010880:Piperidines; D013438:Sulfhydryl Compounds; D013854:Thioamides; D010758:Phosphorus; C032727:piperidine; C078142:bis(2-oxo-3-oxazolidinyl)phosphinic chloride; D011392:Proline; D007930:Leucine