title: Chemoenzymatic synthesis of uridine 5'-diphospho-2-acetonyl-2-deoxy-alpha-D-glucose as C(2)-carbon isostere of UDP-GlcNAc.
abstract: 2-ketoGlc, which is the C(2)-carbon isostere of GlcNAc, is a novel GlcNAc analogue with a ketone group. The corresponding glycosyltransferase donor substrate, UDP-2-ketoGlc, is necessary for synthesizing 2-ketoGlc-containing molecules and is thus highly important for metabolic polysaccharide remodeling and engineering. We report here the first chemoenzymatic synthesis of UDP-2-ketoGlc using our two-enzyme (NahK and GlmU) system in vitro.
authors.affiliation: Department of Chemistry, The Ohio State University, 484 West 12th Avenue, Columbus, Ohio 43210, USA.
authors.forename: Li
authors.initials: L
authors.lastname: Cai
authors.forename: Wanyi
authors.initials: W
authors.lastname: Guan
authors.forename: Wenlan
authors.initials: W
authors.lastname: Chen
authors.forename: Peng George
authors.initials: PG
authors.lastname: Wang
mesh_terms: D055162:Biocatalysis; D015394:Molecular Structure; D009713:Nucleotidyltransferases / Q000737:chemistry / Q000378:metabolism*; D010770:Phosphotransferases / Q000737:chemistry / Q000378:metabolism*; D013237:Stereoisomerism; D014532:Uridine Diphosphate Glucose / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism*; D014537:Uridine Diphosphate N-Acetylglucosamine / Q000031:analogs & derivatives / Q000737:chemistry*
chemical_list: D014537:Uridine Diphosphate N-Acetylglucosamine; D010770:Phosphotransferases; D009713:Nucleotidyltransferases; C023226:UDPacetylglucosamine pyrophosphorylase; D014532:Uridine Diphosphate Glucose
references.citation: FASEB J. 1992 Apr;6(7):2397-404
references.pmid: 1563592
references.citation: Chem Commun (Camb). 2009 Dec 7;(45):6976-8
references.pmid: 19904366
references.citation: J Biol Chem. 1996 Aug 23;271(34):20776-82
references.pmid: 8702831
references.citation: J Am Chem Soc. 2003 Dec 31;125(52):16162-3
references.pmid: 14692737
references.citation: Appl Environ Microbiol. 2007 Oct;73(20):6444-9
references.pmid: 17720833
references.citation: Bioorg Med Chem Lett. 2009 Sep 15;19(18):5433-5
references.pmid: 19683921
references.citation: Org Lett. 2002 Dec 12;4(25):4523-6
references.pmid: 12465928
references.citation: J Am Chem Soc. 2001 Feb 14;123(6):1242-3
references.pmid: 11456684
references.citation: J Am Chem Soc. 2002 Dec 18;124(50):14893-902
references.pmid: 12475330
references.citation: Nat Protoc. 2010 Apr;5(4):636-46
references.pmid: 20224564
references.citation: Chem Commun (Camb). 2009 May 28;(20):2944-6
references.pmid: 19436918
references.citation: Org Lett. 2004 Sep 16;6(19):3217-9
references.pmid: 15355016
references.citation: FEMS Microbiol Rev. 2008 Mar;32(2):168-207
references.pmid: 18266853
references.citation: Proc Natl Acad Sci U S A. 2003 Aug 5;100(16):9116-21
references.pmid: 12874386
references.citation: Glycobiology. 2001 Mar;11(3):25R-36R
references.pmid: 11320055