Chemoenzymatic synthesis of uridine 5'-diphospho-2-acetonyl-2-deoxy-alpha-D-glucose as C(2)-carbon isostere of UDP-GlcNAc.
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.
Cai
Li
L
Department of Chemistry, The Ohio State University, 484 West 12th Avenue, Columbus, Ohio 43210, USA.
Guan
Wanyi
W
Chen
Wenlan
W
Wang
Peng George
PG
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*
D014537:Uridine Diphosphate N-Acetylglucosamine; D010770:Phosphotransferases; D009713:Nucleotidyltransferases; C023226:UDPacetylglucosamine pyrophosphorylase; D014532:Uridine Diphosphate Glucose
FASEB J. 1992 Apr;6(7):2397-404
1563592
Chem Commun (Camb). 2009 Dec 7;(45):6976-8
19904366
J Biol Chem. 1996 Aug 23;271(34):20776-82
8702831
J Am Chem Soc. 2003 Dec 31;125(52):16162-3
14692737
Appl Environ Microbiol. 2007 Oct;73(20):6444-9
17720833
Bioorg Med Chem Lett. 2009 Sep 15;19(18):5433-5
19683921
Org Lett. 2002 Dec 12;4(25):4523-6
12465928
J Am Chem Soc. 2001 Feb 14;123(6):1242-3
11456684
J Am Chem Soc. 2002 Dec 18;124(50):14893-902
12475330
Nat Protoc. 2010 Apr;5(4):636-46
20224564
Chem Commun (Camb). 2009 May 28;(20):2944-6
19436918
Org Lett. 2004 Sep 16;6(19):3217-9
15355016
FEMS Microbiol Rev. 2008 Mar;32(2):168-207
18266853
Proc Natl Acad Sci U S A. 2003 Aug 5;100(16):9116-21
12874386
Glycobiology. 2001 Mar;11(3):25R-36R
11320055