Facile chemoenzymatic synthesis of Lewis a (Lea) antigen in gram-scale and sialyl Lewis a (sLea) antigens containing diverse sialic acid forms

Nova Tasnima, Hai Yu, Xuebin Yan, Wanqing Li, An Xiao, Xi Chen

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

An efficient streamlined chemoenzymatic approach has been developed for gram-scale synthesis of Lewis a angtigen (LeaβProN3) and a library of sialyl Lewis a antigens (sLeaβProN3) containing different sialic acid forms. Intially, commercially available inexpensive N-acetylglucosamine (GlcNAc) was converted to its N′-glycosyl p-toluenesulfonohydrazide in one step. Followed by chemical glycosylation, GlcNAcβProN3 was synthesized using this protecting group-free method in high yield (82%). Sequential one-pot multienzyme (OPME) β1–3-galactosylation of GlcNAcβProN3 followed by OPME α1–4-fucosylation reactions produced target LeaβProN3 in gram-scale. Structurally diverse sialic acid forms was successfully introduced using a OPME sialylation reation containing a CMP-sialic acid synthetase and Pasteurella multocida α2–3-sialyltransferase 1 (PmST1) mutant PmST1 M144D with or without a sialic acid aldolase to form sLeaβProN3 containing naturally occurring or non-natural sialic acid forms in preparative scales.

Original languageEnglish (US)
Pages (from-to)115-121
Number of pages7
JournalCarbohydrate Research
Volume472
DOIs
StatePublished - Jan 15 2019

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N-Acetylneuraminic Acid
Sialyltransferases
Pasteurella multocida
N-acetylneuraminate lyase
Antigens
N-Acylneuraminate Cytidylyltransferase
Glycosylation
Acetylglucosamine
Libraries
5-acetylneuraminyl-2-3-galactosyl-1-3-(fucopyranosyl-1-4)-N-acetylglucosamine

Keywords

  • Chemoenzymatic synthesis
  • Glycosyltransferase
  • Lewis a
  • Protecting group-free glycosylation
  • Sialic acid
  • Sialyl Lewis a

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

Cite this

Facile chemoenzymatic synthesis of Lewis a (Lea) antigen in gram-scale and sialyl Lewis a (sLea) antigens containing diverse sialic acid forms. / Tasnima, Nova; Yu, Hai; Yan, Xuebin; Li, Wanqing; Xiao, An; Chen, Xi.

In: Carbohydrate Research, Vol. 472, 15.01.2019, p. 115-121.

Research output: Contribution to journalArticle

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abstract = "An efficient streamlined chemoenzymatic approach has been developed for gram-scale synthesis of Lewis a angtigen (LeaβProN3) and a library of sialyl Lewis a antigens (sLeaβProN3) containing different sialic acid forms. Intially, commercially available inexpensive N-acetylglucosamine (GlcNAc) was converted to its N′-glycosyl p-toluenesulfonohydrazide in one step. Followed by chemical glycosylation, GlcNAcβProN3 was synthesized using this protecting group-free method in high yield (82{\%}). Sequential one-pot multienzyme (OPME) β1–3-galactosylation of GlcNAcβProN3 followed by OPME α1–4-fucosylation reactions produced target LeaβProN3 in gram-scale. Structurally diverse sialic acid forms was successfully introduced using a OPME sialylation reation containing a CMP-sialic acid synthetase and Pasteurella multocida α2–3-sialyltransferase 1 (PmST1) mutant PmST1 M144D with or without a sialic acid aldolase to form sLeaβProN3 containing naturally occurring or non-natural sialic acid forms in preparative scales.",
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