Gene/Protein Disease Symptom Drug Enzyme Compound
Pivot Concepts:   Target Concepts:
Query: EC:3.2.1.23 (beta-galactosidase)
 14,648 document(s) hit in 31,850,051 MEDLINE articles (0.00 seconds)

Starting from a tumor-associated synthetic MUC1-derived peptide MUC1a' and using a completely enzymatic approach for the synthesis of the core-2 sialyl Lewis X glycopart, the following glycopeptide was synthesized: AHGV[Neu5Ac(alpha2-3)Gal(beta1-4)[Fuc(alpha1-3)]GlcNAc(beta1-6)[Gal(beta1-3)]GalNAc(alpha1-O)]TSAPDTR. First, polypeptide N-acetylgalactosaminyltransferase 3 was used to site-specifically glycosylate MUC1a' to give MUC1a'-GalNAc. Then, in a one-pot reaction employing beta-galactosidase and core-2 beta6-N-acetylglucosaminyltransferase the core-2 O-glycan structure was prepared. The core-2 structure was then sequentially galactosylated, sialylated, and fucosylated by making use of beta4-galactosyltransferase 1, alpha3-sialyltransferase 3, and alpha3-fucosyltransferase 3, respectively, resulting in the sialyl Lewis X glycopeptide. The overall yield of the final compound was 23% (3.2 mg, 1.4 micromol). During the synthesis three intermediate glycopeptides containing O-linked GalNAc, Gal(beta1-4)GlcNAc(beta1-6)[Gal(beta1-3)]GalNAc, and Neu5Ac(alpha2-3)Gal(beta1-4)GlcNAc(beta1-6)[Gal(beta1-3)]GalNAc, respectively, were isolated in mg quantities. All products were characterized by mass spectrometry and NMR spectroscopy.
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PMID:Enzymatic synthesis of the core-2 sialyl Lewis X O-glycan on the tumor-associated MUC1a' peptide. 1277 Jul 66