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An Enzyme Transfers Intact Oligosaccharides

Endo-M is one of the enzymes called endo-β-N-acetylglucosaminidases (endo-β-GlcNAc-ase). This enzyme was found by Yamamoto et al., in the culture fluid of Mucor hiemalis isolated from soil. Endo-M hydrolyzes an N,N-diacetylchitobiose moiety in oligosaccharides bound to the asparaginyl residue of various glycoproteins through the N-glucosidic linkage. The efficacy of this enzyme comes from the fact that one N-acetylglucosamine residue remains bound to the protein while cleaving the N,N-diacetylchitobiose moiety. The enzyme can thus transfer the intact oligosaccharide to suitable receptors.

Haneda et al. have transferred oligosaccharides to 9-fluorenylmethoxycarbonyl-asparaginyl-N-acetylglucosaminide [Fmoc-Asn(GlcNAc)] by incubating sialotransferrin glycopeptide, asialotransferrin glycopeptide and Man6GlcNAc2-Asn-peptide with Endo-M. Furthermore, synthetic hCG (β12-16)-GlcNAc-peptide has been subjected to transglycosylate of sialo complex type oligosaccharides. Inazu et al. have developed an alternative synthetic method for the peptide containing GlcNA. This method uses Fmoc-Asn(GlcNAc) synthesized from N-Fmoc aspartic acid (Fmoc-Asp-OH), and applied to a mixed acid anhydride method using dimethylphosphothioic acid (Mpt-MA), which generally shows poor responses toward hydroxyl groups. By combining this method with Endo-M, many glycopeptides can be designed and easily prepared. Yamamoto has compiled the outline of this methodology as the Chemo-Enzymatic Synthesis in his review. Endo-M can also be used to create new functions by introducing oligosaccharides to substances that originally do not have them. Unlike conventional endo-β-GlcNAc-ase, Endo-M is an enzyme with broad substrate specificity, cleaving not only high mannose type and hybrid type asparagines-linked oligosaccharides in glycoproteins but also performing the transglycosylation reaction of sialo complex type oligosaccharides, a reaction possible only using Endo-M. Therefore, Endo-M is expected to be applied to various fields.


Endo-M (Recombinant : from Mucor hiemalis expressed in Candida boidinii)
[Purity : single band by SDS-PAGE (85KDa)]


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