Chemoenzymatic Synthesis of a Type 2 Blood Group A Tetrasaccharide and Development of High-throughput Assays Enables a Platform for Screening Blood Group Antigen-cleaving Enzymes

Glycobiology

Volumn 25, Issue 8, 2015, Pages 806-811

  Kwan, David H ^a   Ernst, Sabrina ^b   Kötzler, Miriam P ^a   Withers, Stephen G ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

^b RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

Blood group antigen; Enzymatic oligosaccharide synthesis; Glycosyltransferase; Metagenomics

Indexed keywords

ALPHA N ACETYLGALACTOSAMINIDASE; BETA GALACTOSIDASE; BLOOD GROUP A ANTIGEN; BLOOD GROUP ANTIGEN; OLIGOSACCHARIDE; TETRASACCHARIDE; BLOOD GROUP ABO SYSTEM; GLYCOSIDE; HYMECROMONE; RECOMBINANT PROTEIN;

ARTICLE; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME ASSAY; ENZYME SPECIFICITY; ENZYME SYNTHESIS; FLUORESCENCE; HIGH THROUGHPUT SCREENING; METAGENOMICS; PRIORITY JOURNAL; PROTEIN CLEAVAGE; PROTEIN STRUCTURE; BIOASSAY; BIOSYNTHESIS; BLOOD GROUP ABO SYSTEM; CHEMISTRY; ENZYMOLOGY; ESCHERICHIA COLI; GENE EXPRESSION; GENE LIBRARY; GENETICS; HUMAN; METABOLISM; METAGENOME; SYNTHESIS;

ABO BLOOD-GROUP SYSTEM; ALPHA-N-ACETYLGALACTOSAMINIDASE; BETA-GALACTOSIDASE; BIOLOGICAL ASSAY; ESCHERICHIA COLI; FLUORESCENCE; GENE EXPRESSION; GENE LIBRARY; GLYCOSIDES; HIGH-THROUGHPUT SCREENING ASSAYS; HUMANS; HYMECROMONE; METAGENOME; OLIGOSACCHARIDES; RECOMBINANT PROTEINS;

EID: 84928961445     PISSN: 09596658     EISSN: 14602423     Source Type: Journal    
DOI: 10.1093/glycob/cwv031     Document Type: Article

References (48)

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21. Xue M, Guan W, Zou Y, Fang J, Liu X-W, Wang PG, Wang F. 2012. Investigation of the nucleotide triphosphate substrate specificity of Homo sapiens UDP-N-acetylgalactosamine pyrophosphorylase (AGX1). Bioorg Med Chem Lett. 22: 3957-3961.
22. Yi W, Shen J, Zhou G, Li J, Wang PG. 2008. Bacterial homologue of human blood Group A transferase. J Am Chem Soc. 130: 14420-14421.
23. Zähner D, Hakenbeck R. 2000. The Streptococcus pneumoniae beta-galactosidase is a surface protein. J Bacteriol. 182: 5919-5921.
24. Zhao G, Guan W, Cai L, Wang PG. 2010. Enzymatic route to preparative-scale synthesis of UDP-GlcNAc/GalNAc, their analogues and GDP-fucose. Nat Protoc. 5: 636-646.
25. Anderson KM, Ashida H, Maskos K, Dell A, Li S-C, Li Y-T. 2005. A clostridial endo-β-galactosidase that cleaves both blood group A and B glycotypes. J Biol Chem. 280: 7720-7728.
26. Cai L, Guan W, Kitaoka M, Shen J, Xia C, Chen W, Wang PG. 2009. A chemoenzymatic route to N-acetylglucosamine-1-phosphate analogues: substrate specificity investigations of N-acetylhexosamine 1-kinase. Chem Commun. 2944-2946. doi: 10.1039/b904853g
27. Clausen H, Hakomori S. 1989. ABH and related histo-blood group antigens; immunochemical differences in carrier isotypes and their distribution. Vox Sang. 56: 1-20.
28. Dean L. 2005. Blood Groups and Red Cell Antigens. Bethesda, MD: National Center for Biotechnology Information.
29. Engels L, Elling L. 2014. WbgL: a novel bacterial α1,2-fucosyltransferase for the synthesis of 2'-fucosyllactose. Glycobiology. 24: 170-178.
30. Goldstein J, Siviglia G, Hurst R, Lenny L, Reich L. 1982. Group B erythrocytes enzymatically converted to group O survive normally in A, B, and O individuals. Science. 215: 168-170.
31. Higgins MA, Whitworth GE, El Warry N, Randriantsoa M, Samain E, Burke RD, Vocadlo DJ, Boraston AB. 2009. Differential recognition and hydrolysis of host carbohydrate antigens by Streptococcus pneumoniae family 98 glycoside hydrolases. J Biol Chem. 284: 26161-26173.
32. Kajihara Y, Kamiyama D, Yamamoto N, Sakakibara T, Izumi M, Hashimoto H. 2004. Synthesis of 2-[(2-pyridyl)amino]ethyl β-D-lactosaminide and evaluation of its acceptor ability for sialyltransferase: a comparison with 4-methylumbelliferyl and dansyl β-d-lactosaminide. Carbohydr Res. 339: 1545-1550.
33. Katayama T, Sakuma A, Kimura T, Makimura Y, Hiratake J, Sakata K, Yamanoi T, Kumagai H, Yamamoto K. 2004. Molecular cloning and characterization of Bifidobacterium bifidum 1,2-α-L-Fucosidase (AfcA), a novel inverting glycosidase (glycoside hydrolase family 95). J Bacteriol. 186: 4885-4893.
34. Kim Y-W, Lee SS, Warren AJ, Withers SG. 2004a. Directed evolution of a-glycosynthase from Agrobacterium sp. increases its catalytic activity dramatically and expands its substrate repertoire. J Biol Chem. 279: 42787-42798.
35. Kim Y-W, Lee SS, Warren RAJ, Withers SG. 2004b. Directed evolution of a glycosynthase from Agrobacterium sp. increases its catalytic activity dramatically and expands its substrate repertoire. J Biol Chem. 279: 42787-42793.
36. Liu QP, Sulzenbacher G, Yuan H, Bennett EP, Pietz G, Saunders K, Spence J, Nudelman E, Levery SB, White T, et al. 2007. Bacterial glycosidases for the production of universal red blood cells. Nat Biotechnol. 25: 454-464.
37. Liu QP, Yuan H, Bennett EP, Levery SB, Nudelman E, Spence J, Pietz G, Saunders K, White T, Olsson ML, et al. 2008. Identification of a GH110 subfamily of a1,3-galactosidases. J Biol Chem. 283: 8545-8554.
38. Mark BL, Vocadlo DJ, Knapp S, Triggs-Raine BL, Withers SG, James MNG 2001. Crystallographic evidence for substrate-assisted catalysis in a bacterial β-Hexosaminidase. J Biol Chem. 276: 10330-10337.
39. Mark BL, Wasney GA, Salo TJS, Khan AR, Cao Z, Robbins PW, James MNG, Triggs-Raine BL. 1998. Structural and functional characterization of Streptomyces plicatus β-N-Acetylhexosaminidase by comparative molecular modeling and site-directed mutagenesis. J Biol Chem. 273: 19618-19624.
40. Mewis K, Armstrong Z, Song YC, Baldwin SA, Withers SG, Hallam SJ. 2013. Biomining active cellulases from a mining bioremediation system. J Biotechnol. 167: 462-471.
41. Reid ME, Lomas-Francis C, Olsson ML. 2012. The Blood Group Antigen FactsBook. 3rd ed. New York: Elsevier.
42. Singh AK, Pluvinage B, Higgins MA, Dalia AB, Woodiga SA, Flynn M, Lloyd AR, Weiser JN, Stubbs KA, Boraston AB, et al. 2014. Unravelling the multiple functions of the architecturally intricate Streptococcus pneumoniae β-galactosidase, BgaA. PLoS Pathog. 10: e1004364.
43. Studier FW 2005. Protein production by auto-induction in high-density shaking cultures. Protein Expr Purif. 41: 207-234.
44. Wakinaka T, Kiyohara M, Kurihara S, Hirata A, Chaiwangsri T, Ohnuma T, Fukamizo T, Katayama T, Ashida H, Yamamoto K. 2013. Bifidobacterial α-galactosidase with unique carbohydrate-binding module specifically acts on blood group B antigen. Glycobiology. 23: 232-240.
45. Xue M, Guan W, Zou Y, Fang J, Liu X-W, Wang PG, Wang F. 2012. Investigation of the nucleotide triphosphate substrate specificity of Homo sapiens UDP-N-acetylgalactosamine pyrophosphorylase (AGX1). Bioorg Med Chem Lett. 22: 3957-3961.
46. Yi W, Shen J, Zhou G, Li J, Wang PG. 2008. Bacterial homologue of human blood Group A transferase. J Am Chem Soc. 130: 14420-14421.
47. Zähner D, Hakenbeck R. 2000. The Streptococcus pneumoniae beta-galactosidase is a surface protein. J Bacteriol. 182: 5919-5921.
48. Zhao G, Guan W, Cai L, Wang PG. 2010. Enzymatic route to preparative-scale synthesis of UDP-GlcNAc/GalNAc, their analogues and GDP-fucose. Nat Protoc. 5: 636-646.