Chemo- and enzymatic synthesis of partially and fully N-deacetylated 4-methylumbelliferyl chitobiosides

Fluorogenic substrates for chitinase

Yuji Honda, Shinji Tanimori, Mitsunori Kirihata, Satoshi Kaneko, Ken Tokuyasu, Masayuki Hashimoto, Takeshi Watanabe

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Partially and fully N-deacetylated 4-methylumberlliferyl chitobioside (1) derivatives, such as GlcN-GlcNAc-UMB (2), GlcNAc-GlcN-UMB (3), and (GlcN) 2 -UMB (4), were synthesized using chemo- and enzymatic procedure. Fluorescent aglycon was released from the chitobiosides 1, 2 and 3 by the action of chitinase. These UMB glycosides of heterochitobiose were versatile probes for the investigation of substrate binding chitinase from various sources. (C) 2000 Elsevier Science Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)827-829
Number of pages3
JournalBioorganic and Medicinal Chemistry Letters
Volume10
Issue number8
DOIs
Publication statusPublished - 2000 Apr 1

Fingerprint

Chitinases
Fluorescent Dyes
Glycosides
Derivatives
Substrates
4-methylumbelliferyl-chitotrioside
4-O-(N-acetylglucosaminyl)glucosamine
2-amino-2-deoxyglucopyranosyl 2-acetamido-2-deoxyglucopyranose
N,N-diacetylchitobiose

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

Cite this

Honda, Yuji ; Tanimori, Shinji ; Kirihata, Mitsunori ; Kaneko, Satoshi ; Tokuyasu, Ken ; Hashimoto, Masayuki ; Watanabe, Takeshi. / Chemo- and enzymatic synthesis of partially and fully N-deacetylated 4-methylumbelliferyl chitobiosides : Fluorogenic substrates for chitinase. In: Bioorganic and Medicinal Chemistry Letters. 2000 ; Vol. 10, No. 8. pp. 827-829.
@article{9dc133f8c471466895746ca5f86bf4eb,
title = "Chemo- and enzymatic synthesis of partially and fully N-deacetylated 4-methylumbelliferyl chitobiosides: Fluorogenic substrates for chitinase",
abstract = "Partially and fully N-deacetylated 4-methylumberlliferyl chitobioside (1) derivatives, such as GlcN-GlcNAc-UMB (2), GlcNAc-GlcN-UMB (3), and (GlcN) 2 -UMB (4), were synthesized using chemo- and enzymatic procedure. Fluorescent aglycon was released from the chitobiosides 1, 2 and 3 by the action of chitinase. These UMB glycosides of heterochitobiose were versatile probes for the investigation of substrate binding chitinase from various sources. (C) 2000 Elsevier Science Ltd. All rights reserved.",
author = "Yuji Honda and Shinji Tanimori and Mitsunori Kirihata and Satoshi Kaneko and Ken Tokuyasu and Masayuki Hashimoto and Takeshi Watanabe",
year = "2000",
month = "4",
day = "1",
doi = "10.1016/S0960-894X(00)00116-5",
language = "English",
volume = "10",
pages = "827--829",
journal = "Bioorganic and Medicinal Chemistry Letters",
issn = "0960-894X",
publisher = "Elsevier Limited",
number = "8",

}

Chemo- and enzymatic synthesis of partially and fully N-deacetylated 4-methylumbelliferyl chitobiosides : Fluorogenic substrates for chitinase. / Honda, Yuji; Tanimori, Shinji; Kirihata, Mitsunori; Kaneko, Satoshi; Tokuyasu, Ken; Hashimoto, Masayuki; Watanabe, Takeshi.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 10, No. 8, 01.04.2000, p. 827-829.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Chemo- and enzymatic synthesis of partially and fully N-deacetylated 4-methylumbelliferyl chitobiosides

T2 - Fluorogenic substrates for chitinase

AU - Honda, Yuji

AU - Tanimori, Shinji

AU - Kirihata, Mitsunori

AU - Kaneko, Satoshi

AU - Tokuyasu, Ken

AU - Hashimoto, Masayuki

AU - Watanabe, Takeshi

PY - 2000/4/1

Y1 - 2000/4/1

N2 - Partially and fully N-deacetylated 4-methylumberlliferyl chitobioside (1) derivatives, such as GlcN-GlcNAc-UMB (2), GlcNAc-GlcN-UMB (3), and (GlcN) 2 -UMB (4), were synthesized using chemo- and enzymatic procedure. Fluorescent aglycon was released from the chitobiosides 1, 2 and 3 by the action of chitinase. These UMB glycosides of heterochitobiose were versatile probes for the investigation of substrate binding chitinase from various sources. (C) 2000 Elsevier Science Ltd. All rights reserved.

AB - Partially and fully N-deacetylated 4-methylumberlliferyl chitobioside (1) derivatives, such as GlcN-GlcNAc-UMB (2), GlcNAc-GlcN-UMB (3), and (GlcN) 2 -UMB (4), were synthesized using chemo- and enzymatic procedure. Fluorescent aglycon was released from the chitobiosides 1, 2 and 3 by the action of chitinase. These UMB glycosides of heterochitobiose were versatile probes for the investigation of substrate binding chitinase from various sources. (C) 2000 Elsevier Science Ltd. All rights reserved.

UR - http://www.scopus.com/inward/record.url?scp=0034678642&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0034678642&partnerID=8YFLogxK

U2 - 10.1016/S0960-894X(00)00116-5

DO - 10.1016/S0960-894X(00)00116-5

M3 - Article

VL - 10

SP - 827

EP - 829

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

SN - 0960-894X

IS - 8

ER -