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Practical synthesis of novel phosphonopeptides containing Aib P
Author(s) -
CerveraVillanueva Juan Manuel Junior,
ViverosCeballos José Luis,
LinzagaElizalde Irma,
Ordóñez Mario
Publication year - 2016
Publication title -
journal of peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 66
eISSN - 1099-1387
pISSN - 1075-2617
DOI - 10.1002/psc.2841
Subject(s) - chloroformate , racemization , chemistry , yield (engineering) , nucleophilic substitution , nucleophile , combinatorial chemistry , peptide synthesis , organic chemistry , amino acid , catalysis , biochemistry , materials science , metallurgy
Practical and convenient method for the synthesis of novel phosphonopeptides 8a–h and 10a–f incorporating the quaternary α ‐aminophosphonate 6 is reported. The target compounds were prepared in moderate to good yield based on the preparation of the quaternary α ‐aminophosphonate 6 followed by the formation of the α ‐bromoamide 7 and subsequent nucleophilic substitution reaction with several amines or by peptide bond formation with several amino acids and with the quaternary α ‐aminophosphonate 6 , using isobutyl chloroformate as activating agent under racemization‐free condition.