New chemo-enzymatic route toward N-acetylneuraminic acid derivatives with alkyl groups at C-7 hydroxyl group

Jordi Calveras, Yasuhito Nagai, Israt Sultana, Yuji Ueda, Toshinori Higashi, Mitsuru Shoji, Takeshi Sugai

研究成果: Article査読

22 被引用数 (Scopus)

抄録

Based on chemo-enzymatic regio- and stereoselective reactions, new routes toward C-4 substituted N-acetyl-d-mannosamine (ManNAc) and the corresponding sialic acids from d-glucal were established. Lipase-catalyzed regioselective transformation of d-glucal and related substrates furnished precursors on which carbamate and alkyl substituent were properly introduced at C-3 and at C-4, respectively. Cyclic carbamate formation through rhodium-nitrenoid intermediates with iodobenzene pivalate and tert-butyl alcohol proceeded in manno-configured at C-2 as well as α- at C-1, exclusively. Ring opening and deprotection under mild conditions furnished the target ManNAc derivatives, which were the substrates for aldolase-catalyzed reactions.

本文言語English
ページ(範囲)4284-4291
ページ数8
ジャーナルTetrahedron
66
24
DOI
出版ステータスPublished - 2010 6月 12

ASJC Scopus subject areas

  • 生化学
  • 創薬
  • 有機化学

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