Chemo-enzymatic synthesis of imidazolium-tagged sialyllactosamine probes

Imke Sittel; M Carmen Galan

doi:10.1016/j.bmcl.2015.07.049

Chemo-enzymatic synthesis of imidazolium-tagged sialyllactosamine probes

Imke Sittel, M Carmen Galan

Research output: Contribution to journal › Article (Academic Journal) › peer-review

16 Citations (Scopus)

Abstract

Two novel α-linked sialyltrisaccharide imidazolium-type probes (ITags) based on the structures of biologically relevant 6'-sialyllactosamine and 3'-sialyllactosamine were efficiently and stereoselectively prepared using a chemo-enzymatic approach. The apparent kinetic parameters for the enzyme catalyzed transformations with α-2,3-sialyltransferase (α-2,3-ST) and α-2,6-sialyltransferase (α-2,6-ST) were measured by LC-MS using the ionic probes. This strategy demonstrates the suitability of the ITags to probe glycosyltransferase activity and their versatility in the preparation of sialylated epitopes for glycobiology research.

Original language	English
Pages (from-to)	4329-32
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	25
Issue number	19
DOIs	https://doi.org/10.1016/j.bmcl.2015.07.049
Publication status	Published - 1 Oct 2015

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GLYCO-TOOLS: Bio-Inspire Tools for Glycoscience - ERC
Galan, M. C. (Principal Investigator)
1/07/15 → 31/12/20
Project: Research
3-month Core Capability for Chemistry Research
Crosby, J. (Principal Investigator)
1/01/13 → 1/04/13
Project: Research
Reworking of Novel tools for Glycoscience
Galan, M. C. (Principal Investigator)
31/03/12 → 30/08/17
Project: Research

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title = "Chemo-enzymatic synthesis of imidazolium-tagged sialyllactosamine probes",

abstract = "Two novel α-linked sialyltrisaccharide imidazolium-type probes (ITags) based on the structures of biologically relevant 6'-sialyllactosamine and 3'-sialyllactosamine were efficiently and stereoselectively prepared using a chemo-enzymatic approach. The apparent kinetic parameters for the enzyme catalyzed transformations with α-2,3-sialyltransferase (α-2,3-ST) and α-2,6-sialyltransferase (α-2,6-ST) were measured by LC-MS using the ionic probes. This strategy demonstrates the suitability of the ITags to probe glycosyltransferase activity and their versatility in the preparation of sialylated epitopes for glycobiology research.",

author = "Imke Sittel and Galan, {M Carmen}",

year = "2015",

month = oct,

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doi = "10.1016/j.bmcl.2015.07.049",

language = "English",

volume = "25",

pages = "4329--32",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

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TY - JOUR

T1 - Chemo-enzymatic synthesis of imidazolium-tagged sialyllactosamine probes

AU - Sittel, Imke

AU - Galan, M Carmen

PY - 2015/10/1

Y1 - 2015/10/1

N2 - Two novel α-linked sialyltrisaccharide imidazolium-type probes (ITags) based on the structures of biologically relevant 6'-sialyllactosamine and 3'-sialyllactosamine were efficiently and stereoselectively prepared using a chemo-enzymatic approach. The apparent kinetic parameters for the enzyme catalyzed transformations with α-2,3-sialyltransferase (α-2,3-ST) and α-2,6-sialyltransferase (α-2,6-ST) were measured by LC-MS using the ionic probes. This strategy demonstrates the suitability of the ITags to probe glycosyltransferase activity and their versatility in the preparation of sialylated epitopes for glycobiology research.

AB - Two novel α-linked sialyltrisaccharide imidazolium-type probes (ITags) based on the structures of biologically relevant 6'-sialyllactosamine and 3'-sialyllactosamine were efficiently and stereoselectively prepared using a chemo-enzymatic approach. The apparent kinetic parameters for the enzyme catalyzed transformations with α-2,3-sialyltransferase (α-2,3-ST) and α-2,6-sialyltransferase (α-2,6-ST) were measured by LC-MS using the ionic probes. This strategy demonstrates the suitability of the ITags to probe glycosyltransferase activity and their versatility in the preparation of sialylated epitopes for glycobiology research.

U2 - 10.1016/j.bmcl.2015.07.049

DO - 10.1016/j.bmcl.2015.07.049

M3 - Article (Academic Journal)

C2 - 26318990

SN - 0960-894X

VL - 25

SP - 4329

EP - 4332

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 19

ER -

Chemo-enzymatic synthesis of imidazolium-tagged sialyllactosamine probes

Abstract

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Projects

GLYCO-TOOLS: Bio-Inspire Tools for Glycoscience - ERC

3-month Core Capability for Chemistry Research

Reworking of Novel tools for Glycoscience

Cite this