Efficient solid phase peptide synthesis on a phenacyl-resin by a methanesulfonic acid .ALPHA.-amino deprotecting procedure

Autor:	Tooru Kimura, Hiroshi Sakikawa, Kenichi Akaji, Yoshiaki Kiso, Yoichi Fujiwara
Rok vydání:	1990
Předmět:	General Chemistry General Medicine Phenacyl Methanesulfonic acid Combinatorial chemistry Coupling reaction chemistry.chemical_compound chemistry Hexafluorophosphate Drug Discovery Peptide synthesis Organic chemistry Phosphonium Selectivity Derivative (chemistry)
Zdroj:	Chemical and Pharmaceutical Bulletin. 38:270-272
ISSN:	1347-5223 0009-2363
DOI:	10.1248/cpb.38.270
Popis:	We have developed an efficient method for solid phase peptide synthesis which consists of N α -selective deprotection by dilute methanesulfonic acid, in situ neutralization, and rapid coupling reaction using benzotriazol-1-yl-oxy-tris(dimethylamino) phosphonium hexafluorophosphate or new 2-(benzotriazol-1-yl) oxy-1,3-dimethylimidazolidinium hexafluorophosphate. This method was successfully used to synthesize several peptides using a new derivative, Boc-Tyr(Dpp) (Dpp: diphenylphosphinyl) and Boc-Arg(HCl) on a phenacylresin. For this method, we employed a fluoride ion final deprotection strategy based on a two-dimensional orthogonal protection scheme
Databáze:	OpenAIRE
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