The carbenoid approach to peptide synthesis.
Chemistry
; 6(12): 2160-7, 2000 Jun 16.
Article
em En
| MEDLINE
| ID: mdl-10926221
ABSTRACT
A different approach to the synthesis of dipeptides is described based on the formation of the NHCHR1CONH-CHR2CO bond by carbenoid N-H insertion, rather than the formation of the peptide bond itself. Thus decomposition of triethyl diazophosphonoacetate catalysed by rhodium(II) acetate in the presence of N-protected amino acid amides 8 gives the phosphonates 9. Subsequent Wadsworth-Emmons reaction of 9 with aldehydes in the presence of DBU gives dehydro dipeptides 10. The reaction has been extended to a simple two-step procedure, without the isolation of the intermediate phosphonate, for conversion of a range of amino acid amides 11 into dehydro dipeptides 12 and to an N-methylamide 11 h, and for conversion of a dipeptide to tripeptide (13-->14). Direct conversion, by using methyl diazophenylacetate, of amino acid amides to phenylglycine-containing dipeptides 19 proceeds in good chemical yield, but with poor diastereoselectivity.
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Base de dados:
MEDLINE
Assunto principal:
Biossíntese Peptídica
/
Amidas
Idioma:
En
Ano de publicação:
2000
Tipo de documento:
Article