Chemoenzymatic synthesis of sialosides and their applications

Hai Yu, Harshal A. Chokhawala, Shengshu Huang, Xi Chen

Research output: Chapter in Book/Report/Conference proceedingConference contribution

1 Citation (Scopus)

Abstract

Recent progress in the development of efficient one-pot three- enzyme chemoenzymatic synthesis and application of functionalized sialosides is described. By taking the advantage of relaxed substrate specificity of several bacterial sialoside biosynthetic enzymes, the method has been used for the prepactive scale synthesis of α2,3- and α2,6-linked sialoside libraries containing naturally and non-naturally occurring sialic acid modifications. Starting from the hexose precursors (ManNAc or mannose) of sialic acids, a library of pNP-tagged sialyl disaccharides with various naturally occurring sialic acid forms, different sialyl linkages, and different penultimate monosaccharides have also been prepared and used in the substrate specificity studies of bacterial sialidases in a 96-well plate-based colorimetric high-throughput screening platform. The combination of efficient chemoenzymatic synthesis and high-throughput screening is a powerful approach to studying proteins that recognizing sialic acid-containing carbohydrates.

Original languageEnglish (US)
Title of host publicationACS Symposium Series
PublisherAmerican Chemical Society
Pages96-122
Number of pages27
Volume990
ISBN (Print)9780841274402
DOIs
StatePublished - Sep 1 2008

Publication series

NameACS Symposium Series
Volume990
ISSN (Print)00976156
ISSN (Electronic)19475918

Fingerprint

N-Acetylneuraminic Acid
Acids
Screening
Throughput
Sialic Acids
Hexoses
Enzymes
Monosaccharides
Disaccharides
Substrates
Mannose
Carbohydrates
Proteins

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

Cite this

Yu, H., Chokhawala, H. A., Huang, S., & Chen, X. (2008). Chemoenzymatic synthesis of sialosides and their applications. In ACS Symposium Series (Vol. 990, pp. 96-122). (ACS Symposium Series; Vol. 990). American Chemical Society. https://doi.org/10.1021/bk-2008-0990.ch005

Chemoenzymatic synthesis of sialosides and their applications. / Yu, Hai; Chokhawala, Harshal A.; Huang, Shengshu; Chen, Xi.

ACS Symposium Series. Vol. 990 American Chemical Society, 2008. p. 96-122 (ACS Symposium Series; Vol. 990).

Research output: Chapter in Book/Report/Conference proceedingConference contribution

Yu, H, Chokhawala, HA, Huang, S & Chen, X 2008, Chemoenzymatic synthesis of sialosides and their applications. in ACS Symposium Series. vol. 990, ACS Symposium Series, vol. 990, American Chemical Society, pp. 96-122. https://doi.org/10.1021/bk-2008-0990.ch005
Yu H, Chokhawala HA, Huang S, Chen X. Chemoenzymatic synthesis of sialosides and their applications. In ACS Symposium Series. Vol. 990. American Chemical Society. 2008. p. 96-122. (ACS Symposium Series). https://doi.org/10.1021/bk-2008-0990.ch005
Yu, Hai ; Chokhawala, Harshal A. ; Huang, Shengshu ; Chen, Xi. / Chemoenzymatic synthesis of sialosides and their applications. ACS Symposium Series. Vol. 990 American Chemical Society, 2008. pp. 96-122 (ACS Symposium Series).
@inproceedings{b21f2337fcdf431cbe3d1b62d857b7f3,
title = "Chemoenzymatic synthesis of sialosides and their applications",
abstract = "Recent progress in the development of efficient one-pot three- enzyme chemoenzymatic synthesis and application of functionalized sialosides is described. By taking the advantage of relaxed substrate specificity of several bacterial sialoside biosynthetic enzymes, the method has been used for the prepactive scale synthesis of α2,3- and α2,6-linked sialoside libraries containing naturally and non-naturally occurring sialic acid modifications. Starting from the hexose precursors (ManNAc or mannose) of sialic acids, a library of pNP-tagged sialyl disaccharides with various naturally occurring sialic acid forms, different sialyl linkages, and different penultimate monosaccharides have also been prepared and used in the substrate specificity studies of bacterial sialidases in a 96-well plate-based colorimetric high-throughput screening platform. The combination of efficient chemoenzymatic synthesis and high-throughput screening is a powerful approach to studying proteins that recognizing sialic acid-containing carbohydrates.",
author = "Hai Yu and Chokhawala, {Harshal A.} and Shengshu Huang and Xi Chen",
year = "2008",
month = "9",
day = "1",
doi = "10.1021/bk-2008-0990.ch005",
language = "English (US)",
isbn = "9780841274402",
volume = "990",
series = "ACS Symposium Series",
publisher = "American Chemical Society",
pages = "96--122",
booktitle = "ACS Symposium Series",

}

TY - GEN

T1 - Chemoenzymatic synthesis of sialosides and their applications

AU - Yu, Hai

AU - Chokhawala, Harshal A.

AU - Huang, Shengshu

AU - Chen, Xi

PY - 2008/9/1

Y1 - 2008/9/1

N2 - Recent progress in the development of efficient one-pot three- enzyme chemoenzymatic synthesis and application of functionalized sialosides is described. By taking the advantage of relaxed substrate specificity of several bacterial sialoside biosynthetic enzymes, the method has been used for the prepactive scale synthesis of α2,3- and α2,6-linked sialoside libraries containing naturally and non-naturally occurring sialic acid modifications. Starting from the hexose precursors (ManNAc or mannose) of sialic acids, a library of pNP-tagged sialyl disaccharides with various naturally occurring sialic acid forms, different sialyl linkages, and different penultimate monosaccharides have also been prepared and used in the substrate specificity studies of bacterial sialidases in a 96-well plate-based colorimetric high-throughput screening platform. The combination of efficient chemoenzymatic synthesis and high-throughput screening is a powerful approach to studying proteins that recognizing sialic acid-containing carbohydrates.

AB - Recent progress in the development of efficient one-pot three- enzyme chemoenzymatic synthesis and application of functionalized sialosides is described. By taking the advantage of relaxed substrate specificity of several bacterial sialoside biosynthetic enzymes, the method has been used for the prepactive scale synthesis of α2,3- and α2,6-linked sialoside libraries containing naturally and non-naturally occurring sialic acid modifications. Starting from the hexose precursors (ManNAc or mannose) of sialic acids, a library of pNP-tagged sialyl disaccharides with various naturally occurring sialic acid forms, different sialyl linkages, and different penultimate monosaccharides have also been prepared and used in the substrate specificity studies of bacterial sialidases in a 96-well plate-based colorimetric high-throughput screening platform. The combination of efficient chemoenzymatic synthesis and high-throughput screening is a powerful approach to studying proteins that recognizing sialic acid-containing carbohydrates.

UR - http://www.scopus.com/inward/record.url?scp=84905592890&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84905592890&partnerID=8YFLogxK

U2 - 10.1021/bk-2008-0990.ch005

DO - 10.1021/bk-2008-0990.ch005

M3 - Conference contribution

SN - 9780841274402

VL - 990

T3 - ACS Symposium Series

SP - 96

EP - 122

BT - ACS Symposium Series

PB - American Chemical Society

ER -