title: Safe and efficient Boc-SPPS for the synthesis of glycopeptide-α-thioesters.
abstract: 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.
authors.affiliation: Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka, 560-0043, Japan.
authors.forename: Masayuki
authors.initials: M
authors.lastname: Izumi
authors.affiliation: Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka, 560-0043, Japan.
authors.forename: Masumi
authors.initials: M
authors.lastname: Murakami
authors.affiliation: Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka, 560-0043, Japan.
authors.forename: Ryo
authors.initials: R
authors.lastname: Okamoto
authors.affiliation: Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka, 560-0043, Japan.|Japan Science and Technology Agency (JST), ERATO, Ito Glycotrilogy Project, 2-1 Hirosawa, Wako, Saitama, 351-0198, Japan.
authors.forename: Yasuhiro
authors.initials: Y
authors.lastname: Kajihara
mesh_terms: D000215:Acylation; D002851:Chromatography, High Pressure Liquid; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D006020:Glycopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D060327:Solid-Phase Synthesis Techniques / Q000379:methods*; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D004952:Esters; D006020:Glycopeptides; D013438:Sulfhydryl Compounds
keywords: glycopeptide‐ α ‐thioester; oligosaccharide; safety Boc‐solid phase peptide synthesis; sialic acid; thiolysis