Synthesis of an ether-linked alkyl 5a-carba-β-D-glucoside, a 5a-carba-β-D-galactoside, a 2-acetamido-2-deoxy-5a-carba-β-D-glucoside, and an alkyl 5a′-carba-β-lactoside

Seiichiro Ogawa, Hiroshi Aoyama, Toshinori Sato

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

For the purpose of providing biologically stable building blocks for the biocombinatorial synthesis using a living cell, some ether-linked alkyl 5a-carba-β-D-glycoside primers were prepared. The key step of the synthesis was coupling of 1-bromo-n-alkanes with the 1-OH unprotected derivatives of 5a-carba-sugar analogues of D-glucose, D-galactose, and 2-acetamido-2-deoxy-D-glucose (N-acetyl-D-glucosamine), in DMF in the presence of sodium hydride. Alternatively, alkyl carba-lactoside was synthesized by incorporation of a 5a-carba-β-D-galactose residue into the 4-position of dodecyl β-D-glucopyranoside. A strong and specific inhibition of β-galactosidase (Ki 0.67 μM, bovine liver) was found for dodecyl 5a-carba-β-D-galactopyranoside.

Original languageEnglish
Pages (from-to)1979-1992
Number of pages14
JournalCarbohydrate Research
Volume337
Issue number21-23
DOIs
Publication statusPublished - 2002 Nov 19

Fingerprint

Galactosides
Acetylglucosamine
Glucosides
Galactose
Ether
Carbasugars
Galactosidases
Alkanes
Glycosides
Liver
Cells
Derivatives
Glucose
lactosides
sodium hydride

Keywords

  • β-Galactosidase inhibitor
  • Alkyl 5a-carba-glycosides, ether-linked
  • Biocombinatorial synthesis using a living cell
  • Carba-sugars
  • Sugar mimics

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

Synthesis of an ether-linked alkyl 5a-carba-β-D-glucoside, a 5a-carba-β-D-galactoside, a 2-acetamido-2-deoxy-5a-carba-β-D-glucoside, and an alkyl 5a′-carba-β-lactoside. / Ogawa, Seiichiro; Aoyama, Hiroshi; Sato, Toshinori.

In: Carbohydrate Research, Vol. 337, No. 21-23, 19.11.2002, p. 1979-1992.

Research output: Contribution to journalArticle

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