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Synthesis of Met‐enkephalin by solution‐phase peptide synthesis methodology utilizing para ‐toluene sulfonic acid as N‐terminal masking of l ‐methionine amino acid
Author(s) -
Khan Riaz A.
Publication year - 2016
Publication title -
chemical biology and drug design
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.59
H-Index - 77
eISSN - 1747-0285
pISSN - 1747-0277
DOI - 10.1111/cbdd.12821
Subject(s) - pentapeptide repeat , chemistry , peptide synthesis , amino acid , methionine , peptide , protecting group , phenylalanine , sulfonic acid , toluene , stereochemistry , combinatorial chemistry , organic chemistry , biochemistry , alkyl
The Met‐enkephalin, Tyr‐Gly‐Gly‐Phe‐Met, was synthesized by the solution‐phase synthesis (SPS) methodology employing ‐OBzl group as carboxyls' protection, while the t ‐Boc groups were employed for the N‐terminal α ‐amines' protection for the majority of the amino acids of the pentapeptide sequence. The l ‐methionine ( l ‐Met) amino acid was used as PTSA.Met‐OBzl obtained from the simultaneous protection of the α ‐amino, and carboxyl group with para ‐toluene sulfonic acid (PTSA) and as‐OBzl ester, respectively in a C‐terminal start of the 2 + 2 + 1 fragments condensation convergent synthetic approach. The protection strategy provided a short, single‐step, simultaneous, orthogonal, nearly quantitative, robust, and stable process to carry through the protected l ‐methionine and l ‐phenylalanine coupling without any structural deformities during coupling and workups. The structurally confirmed final pentapeptide product was feasibly obtained in good yields through the current approach.