6-Azido-6-deoxy-l-idose as a Hetero-Bifunctional Spacer for the Synthesis of Azido-Containing Chemical Probes

Hiroki Hamagami, Motofumi Kumazoe, Yoshiki Yamaguchi, Shinichiro Fuse, Hirofumi Tachibana, Hiroshi Tanaka

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

The design of 6-azido-6-deoxy-l-idose for use as a hetero-bifunctional spacer is reported. The hemiacetal at one terminus is an equivalent of an aldehyde and can react with nucleophiles, such as amino groups and electron-rich aromatics. The azido group at the other terminus bio-orthogonally undergoes a Hüisgen [3+2] cycloaddition with an acetylene. The idose derivative exhibited a higher level of reactivity towards oxime formation than a corresponding glucose derivative. The13C NMR spectrum of the uniformly13C-labeled 6-azido-idose indicated that the acyclic forms of the sugar totaled 0.3 % of all the isomers, whereas those of glucose totaled 0.01 %. The larger population of the acyclic forms of the idose derivative would result in higher reactivity towards electrophilic addition in comparison with glucose derivatives. Finally, we prepared a C-idosyl epigallocatechin gallate (EGCG) that bears an azido group through C-glycosylation of EGCG with 6-azido-idose. This glycosyl form of the C-idosyl EGCG exhibited a cytotoxicity against U266 cells that was comparable to that of EGCG. These results suggested that the EGCG derivative could be used as an effective chemical probe for the elucidation of EGCG biological functions.

Original languageEnglish
Pages (from-to)12884-12890
Number of pages7
JournalChemistry - A European Journal
Volume22
Issue number36
DOIs
Publication statusPublished - Jan 1 2016

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Derivatives
Glucose
Glycosylation
Nucleophiles
Cycloaddition
Acetylene
Cytotoxicity
Aldehydes
Oximes
Sugars
Isomers
Nuclear magnetic resonance
epigallocatechin gallate
idose
Electrons

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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6-Azido-6-deoxy-l-idose as a Hetero-Bifunctional Spacer for the Synthesis of Azido-Containing Chemical Probes. / Hamagami, Hiroki; Kumazoe, Motofumi; Yamaguchi, Yoshiki; Fuse, Shinichiro; Tachibana, Hirofumi; Tanaka, Hiroshi.

In: Chemistry - A European Journal, Vol. 22, No. 36, 01.01.2016, p. 12884-12890.

Research output: Contribution to journalArticle

Hamagami, Hiroki ; Kumazoe, Motofumi ; Yamaguchi, Yoshiki ; Fuse, Shinichiro ; Tachibana, Hirofumi ; Tanaka, Hiroshi. / 6-Azido-6-deoxy-l-idose as a Hetero-Bifunctional Spacer for the Synthesis of Azido-Containing Chemical Probes. In: Chemistry - A European Journal. 2016 ; Vol. 22, No. 36. pp. 12884-12890.
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