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Safe and efficient Boc‐SPPS for the synthesis of glycopeptide‐α‐thioesters
Author(s) -
Izumi Masayuki,
Murakami Masumi,
Okamoto Ryo,
Kajihara Yasuhiro
Publication year - 2014
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.2608
Subject(s) - thioester , chemistry , glycopeptide , linker , peptide , combinatorial chemistry , peptide synthesis , solid phase synthesis , native chemical ligation , organic chemistry , cysteine , biochemistry , enzyme , operating system , computer science , antibiotics
Boc‐solid phase peptide synthesis is useful for the preparation of peptide‐ α ‐thioesters. However, this strategy usually employs hydrogen fluoride for the final deprotection step. These strongly acidic conditions cannot be applied for the synthesis of acid‐labile glycopeptide‐ α ‐thioesters. The protocol presented here is a modified in situ neutralization Boc‐solid phase peptide synthesis employing 10% sulfuric acid/dioxane conditions for intermediate Boc removal and TfOH for the final side‐chain deprotection step. These conditions were found to be applicable for the synthesis of acid‐labile glycopeptide‐ α ‐thioesters. In this protocol, a glycopeptide is synthesized as α ‐ thioester on a thiol linker, and the product glycopeptide‐ α ‐thioester is released from the resin by thiolysis after side‐chain deprotection step with an acid cocktail containing TfOH instead of hydrogen fluoride. Copyright © 2014 European Peptide Society and John Wiley & Sons, Ltd.