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Enzymic synthesis of the trisaccharide core region of the carbohydrate chain ofN-glycoprotein

Abstract

Transmannosylation from mannotriose (Manβ1-4Manβ1-4Man) to the 4-position at the nonreducing end N-acetylglucosaminyl residue ofN,N′-diacetylchitobiose was regioselectively induced through the use of β-d-mannanase fromAspergillus niger. The enzyme formed the trisaccharide Manβ1-4GlcNAcβ1-4GlcNAc (3.7% of the enzyme-catalysed net decrease ofN,N′-diacetylchitobiose) from mannotriose as a donor andN,N′-diacetylchitobiose as an acceptor. Mannobiose (Manβ1-4Man) was also shown to be useful as a donor substrate for the desired trisaccharide synthesis.

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Abbreviations

Man:

d-mannose

(M n) (n=1−5):

β-linkedn-mer of mannose

GlcNAc2 :

2-acetamido-2-deoxy-β-d-glucopyranosyl-(1–4)-2-acetamido-2-deoxy-d-glucose

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Correspondence to Taichi Usui.

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Usui, T., Suzuki, M., Sato, T. et al. Enzymic synthesis of the trisaccharide core region of the carbohydrate chain ofN-glycoprotein. Glycoconjugate J 11, 105–110 (1994). https://doi.org/10.1007/BF00731150

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Keywords

  • Manβ1-4GlcNAcβ1-4GlcNAc
  • β-d-mannanase in carbohydrate synthesis
  • trisaccharide core ofN-glycoprotein