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Nitroacetyl Group as a Peptide Synthon: Synthesis of Dipeptides with an α,α‐Bisallylglycine Residue at the N‐Terminus
Author(s) -
Manjunatha Sulur G.,
Chittari Pabba,
Rajappa Srinivasachari
Publication year - 1991
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19910740516
Subject(s) - chemistry , synthon , residue (chemistry) , protecting group , yield (engineering) , valine , glycine , stereochemistry , phenylalanine , peptide , proline , catalysis , dipeptide , amino acid , medicinal chemistry , organic chemistry , alkyl , materials science , metallurgy , biochemistry
N ‐Nitroacetyl derivatives of L‐proline, L‐valine, and L‐phenylalanine esters were prepared in two steps under mild conditions ( Scheme 2 ). Regiospecific mono‐ and bis‐allylation of these nitroacetyl derivatives were accomplished in presence of a Pd(0) catalyst. The bis‐allyl derivatives 7–9 were obtained in 40–75% yield. The tertiary NO 2 group in these compounds could be transformed into an acetylamino group by Zn/AcOH/Ac 2 O. The final products 11–13 are dipeptides in which the N‐terminal glycine residue bears two α‐allyl substituents.