Carbohydrate Research

, volume 329 , issue 3 , pages 539-547

The synthesis, testing and use of 5-fluoro-α-d-galactosyl fluoride to trap an intermediate on green coffee bean α-galactosidase and identify the catalytic nucleophile

Hoa D. Ly ¹

S. K. Howard ²

Kelly Shum ²

Shouming HE ²

Alex Zhu ³

STEPHEN G. WITHERS ²

Hide authors affiliations Show authors affiliations: 3 affiliations

Department of Chemistry, University of British Columbia,Vancouver, BC, Canada |

Department of Chemistry, University of British Columbia, Vancouver,
BC, Canada V6T 1Z1 |

The Lindsley F. Kimball Research Institute of the New York Blood Center, New York, NY 10021, USA. |

Publication type: Journal Article

Publication date: 2000-11-01

Elsevier

Carbohydrate Research

scimago Q3

wos Q2

SJR: 0.423

CiteScore: 4.0

Impact factor: 2.5

ISSN: 00086215, 1873426X

DOI: 10.1016/S0008-6215(00)00214-7

Copy DOI

PubMed ID: 11128583

Organic Chemistry

Biochemistry

General Medicine

Analytical Chemistry

Abstract

5-Fluoro-alpha-D-galactopyranosyl fluoride was synthesized and its interaction with the active site of an alpha-galactosidase from green coffee bean (Coffea arabica), a retaining glycosidase, characterized kinetically and structurally. The compound behaves as an apparently tight binding (Ki = 600 nM) competitive inhibitor, achieving this high affinity through reaction as a slow substrate that accumulates a high steady-state concentration of the glycosyl-enzyme intermediate, as evidenced by ESiMS. Proteolysis of the trapped enzyme coupled with HPLC/MS analysis allowed the localization of a labeled peptide that was subsequently sequenced. Comparison of this sequence information to that of other members of the same glycosidase family revealed the active site nucleophile to be Asp145 within the sequence LKYDNCNNN. The importance of this residue to catalysis has been confirmed by mutagenesis studies.

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GOST |

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GOST Copy

Ly H. D. et al. The synthesis, testing and use of 5-fluoro-α-d-galactosyl fluoride to trap an intermediate on green coffee bean α-galactosidase and identify the catalytic nucleophile // Carbohydrate Research. 2000. Vol. 329. No. 3. pp. 539-547.

GOST all authors (up to 50) Copy

Ly H. D., Howard S. K., Shum K., HE S., Zhu A., WITHERS S. G. The synthesis, testing and use of 5-fluoro-α-d-galactosyl fluoride to trap an intermediate on green coffee bean α-galactosidase and identify the catalytic nucleophile // Carbohydrate Research. 2000. Vol. 329. No. 3. pp. 539-547.

RIS |

Cite this

RIS Copy

TY - JOUR

DO - 10.1016/S0008-6215(00)00214-7

UR - https://doi.org/10.1016/S0008-6215(00)00214-7

TI - The synthesis, testing and use of 5-fluoro-α-d-galactosyl fluoride to trap an intermediate on green coffee bean α-galactosidase and identify the catalytic nucleophile

T2 - Carbohydrate Research

AU - Ly, Hoa D.

AU - Howard, S. K.

AU - Shum, Kelly

AU - HE, Shouming

AU - Zhu, Alex

AU - WITHERS, STEPHEN G.

PY - 2000

DA - 2000/11/01

PB - Elsevier

SP - 539-547

IS - 3

VL - 329

PMID - 11128583

SN - 0008-6215

SN - 1873-426X

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2000_Ly,

author = {Hoa D. Ly and S. K. Howard and Kelly Shum and Shouming HE and Alex Zhu and STEPHEN G. WITHERS},

title = {The synthesis, testing and use of 5-fluoro-α-d-galactosyl fluoride to trap an intermediate on green coffee bean α-galactosidase and identify the catalytic nucleophile},

journal = {Carbohydrate Research},

year = {2000},

volume = {329},

publisher = {Elsevier},

month = {nov},

url = {https://doi.org/10.1016/S0008-6215(00)00214-7},

number = {3},

pages = {539--547},

doi = {10.1016/S0008-6215(00)00214-7}

}

MLA

Cite this

MLA Copy

Ly, Hoa D., et al. “The synthesis, testing and use of 5-fluoro-α-d-galactosyl fluoride to trap an intermediate on green coffee bean α-galactosidase and identify the catalytic nucleophile.” Carbohydrate Research, vol. 329, no. 3, Nov. 2000, pp. 539-547. https://doi.org/10.1016/S0008-6215(00)00214-7.

Publisher

Elsevier

Journal

Carbohydrate Research

scimago Q3

wos Q2

SJR

0.423

CiteScore

4.0

Impact factor

2.5

ISSN

00086215 (Print)

1873426X (Electronic)

Profiles

Stephen G Withers