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Design and synthesis of silyl ether-based linker for solid-phase synthesis of glycopeptides

โœ Scribed by Kazuhiko Nakamura; Noriyasu Hanai; Masayuki Kanno; Aki Kobayashi; Yuki Ohnishi; Yukishige Ito; Yoshiaki Nakahara

Book ID
104260418
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
211 KB
Volume
40
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

A novel silyl linker was designed to facilitate the solid-phase synthesis of protected glycopeptide blocks. Alcohols (carbohydrate, serine, or threonine) were silylated with trialkylchlorosilane containing the p-nitrophenyl group. The nitro group was reduced and succinylated to give the succinanilic acids, which were attached to the glycine-preloaded resin via activation with HBTU/HOBt. After elongation of the peptide chain by segment condensation or Fmoc chemistry-based stepwise method, the synthesized glycopeptides in the protected form were split from the resin by fluoridolysis.

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