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Alternative Procedures for the Synthesis of Methionine‐Containing Peptide−Oligonucleotide Hybrids
Author(s) -
Marchán Vicente,
RodríguezTanty Chryslaine,
Estrada Marta,
Pedroso Enrique,
Grandas Anna
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200007)2000:13<2495::aid-ejoc2495>3.0.co;2-t
Subject(s) - thioether , chemistry , methionine sulfoxide , oligonucleotide , methionine , sulfoxide , peptide , peptide synthesis , combinatorial chemistry , solid phase synthesis , amino acid , organic chemistry , biochemistry , stereochemistry , dna
Abstract The synthesis of methionine‐containing peptide−oligonucleotide hybrids has been found to be best accomplished by a stepwise solid‐phase approach in which peptide assembly using the sulfoxide derivative of methionine is followed by elongation of the oligonucleotide chain using the phosphite triester methodology, ammonia deprotection, and reduction of the sulfoxide to thioether by reaction with N ‐methylmercaptoacetamide. Quantitative amino acid incorporation yields could not always be achieved when the order of assembly of the two moieties was reversed, i.e. by elongating the peptide chain on a resin‐linked oligonucleotide in order to avoid exposure of the thioether function to oxidizing conditions.