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

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)4284-4291
Number of pages8
JournalTetrahedron
Volume66
Issue number24
DOIs
Publication statusPublished - 2010 Jun 12

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Carbamates
N-Acetylneuraminic Acid
Hydroxyl Radical
tert-Butyl Alcohol
Sialic Acids
Derivatives
Rhodium
Fructose-Bisphosphate Aldolase
Substrates
Lipase
d-glucal
mannosamine
iodobenzene

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

New chemo-enzymatic route toward N-acetylneuraminic acid derivatives with alkyl groups at C-7 hydroxyl group. / Calveras, Jordi; Nagai, Yasuhito; Sultana, Israt; Ueda, Yuji; Higashi, Toshinori; Shoji, Mitsuru; Sugai, Takeshi.

In: Tetrahedron, Vol. 66, No. 24, 12.06.2010, p. 4284-4291.

Research output: Contribution to journalArticle

Calveras, Jordi ; Nagai, Yasuhito ; Sultana, Israt ; Ueda, Yuji ; Higashi, Toshinori ; Shoji, Mitsuru ; Sugai, Takeshi. / New chemo-enzymatic route toward N-acetylneuraminic acid derivatives with alkyl groups at C-7 hydroxyl group. In: Tetrahedron. 2010 ; Vol. 66, No. 24. pp. 4284-4291.
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AU - Sugai, Takeshi

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