Efficient Enzymatic Synthesis of Guanosine 5'-diphosphate-sugars and Derivatives

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2013 Oct 15

PMID 24117142

Citations 16

Authors

Lei Li

Yonghui Liu

Yue Wan

Yanhong Li

Xi Chen

Wei Zhao

Peng George Wang

Affiliations

Soon will be listed here.

Abstract

An N-acetylhexosamine 1-kinase from Bifidobacterium infantis (NahK_15697), a guanosine 5'-diphosphate (GDP)-mannose pyrophosphorylase from Pyrococcus furiosus (PFManC), and an Escherichia coli inorganic pyrophosphatase (EcPpA) were used efficiently for a one-pot three-enzyme synthesis of GDP-mannose, GDP-glucose, their derivatives, and GDP-talose. This study represents the first facile and efficient enzymatic synthesis of GDP-sugars and derivatives starting from monosaccharides and derivatives.

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References

Guan W, Cai L, Fang J, Wu B, Wang P . Enzymatic synthesis of UDP-GlcNAc/UDP-GalNAc analogs using N-acetylglucosamine 1-phosphate uridyltransferase (GlmU). Chem Commun (Camb). 2009; (45):6976-8. DOI: 10.1039/b917573c. View

Schoenhofen I, Vinogradov E, Whitfield D, Brisson J, Logan S . The CMP-legionaminic acid pathway in Campylobacter: biosynthesis involving novel GDP-linked precursors. Glycobiology. 2009; 19(7):715-25. DOI: 10.1093/glycob/cwp039. View

Muthana M, Qu J, Li Y, Zhang L, Yu H, Ding L . Efficient one-pot multienzyme synthesis of UDP-sugars using a promiscuous UDP-sugar pyrophosphorylase from Bifidobacterium longum (BLUSP). Chem Commun (Camb). 2012; 48(21):2728-30. DOI: 10.1039/c2cc17577k. View

Samuel G, Reeves P . Biosynthesis of O-antigens: genes and pathways involved in nucleotide sugar precursor synthesis and O-antigen assembly. Carbohydr Res. 2003; 338(23):2503-19. DOI: 10.1016/j.carres.2003.07.009. View

Cai L, Guan W, Wang W, Zhao W, Kitaoka M, Shen J . Substrate specificity of N-acetylhexosamine kinase towards N-acetylgalactosamine derivatives. Bioorg Med Chem Lett. 2009; 19(18):5433-5. DOI: 10.1016/j.bmcl.2009.07.104. View

Loibl M, Strahl S . Protein O-mannosylation: what we have learned from baker's yeast. Biochim Biophys Acta. 2013; 1833(11):2438-46. DOI: 10.1016/j.bbamcr.2013.02.008. View

Kleczkowski L, Decker D, Wilczynska M . UDP-sugar pyrophosphorylase: a new old mechanism for sugar activation. Plant Physiol. 2011; 156(1):3-10. PMC: 3091059. DOI: 10.1104/pp.111.174706. View

Carpita N . Update on mechanisms of plant cell wall biosynthesis: how plants make cellulose and other (1->4)-β-D-glycans. Plant Physiol. 2010; 155(1):171-84. PMC: 3075763. DOI: 10.1104/pp.110.163360. View

Goto M . Protein O-glycosylation in fungi: diverse structures and multiple functions. Biosci Biotechnol Biochem. 2007; 71(6):1415-27. DOI: 10.1271/bbb.70080. View

10.

Marchesan S, Macmillan D . Chemoenzymatic synthesis of GDP-azidodeoxymannoses: non-radioactive probes for mannosyltransferase activity. Chem Commun (Camb). 2008; (36):4321-3. DOI: 10.1039/b807016d. View

11.

Lahti R, Pitkaranta T, Valve E, Ilta I, Heinonen J . Cloning and characterization of the gene encoding inorganic pyrophosphatase of Escherichia coli K-12. J Bacteriol. 1988; 170(12):5901-7. PMC: 211699. DOI: 10.1128/jb.170.12.5901-5907.1988. View

12.

Nishimoto M, Kitaoka M . Identification of N-acetylhexosamine 1-kinase in the complete lacto-N-biose I/galacto-N-biose metabolic pathway in Bifidobacterium longum. Appl Environ Microbiol. 2007; 73(20):6444-9. PMC: 2075035. DOI: 10.1128/AEM.01425-07. View

13.

Li Y, Yu H, Chen Y, Lau K, Cai L, Cao H . Substrate promiscuity of N-acetylhexosamine 1-kinases. Molecules. 2011; 16(8):6396-407. PMC: 6264712. DOI: 10.3390/molecules16086396. View

14.

Costa J, Empadinhas N, da Costa M . Glucosylglycerate biosynthesis in the deepest lineage of the Bacteria: characterization of the thermophilic proteins GpgS and GpgP from Persephonella marina. J Bacteriol. 2006; 189(5):1648-54. PMC: 1855766. DOI: 10.1128/JB.00841-06. View

15.

Coyne M, Reinap B, Lee M, Comstock L . Human symbionts use a host-like pathway for surface fucosylation. Science. 2005; 307(5716):1778-81. DOI: 10.1126/science.1106469. View

16.

Wagner G, Pesnot T, Field R . A survey of chemical methods for sugar-nucleotide synthesis. Nat Prod Rep. 2009; 26(9):1172-94. DOI: 10.1039/b909621n. View

17.

Wang W, Hu T, Frantom P, Zheng T, Gerwe B, Del Amo D . Chemoenzymatic synthesis of GDP-L-fucose and the Lewis X glycan derivatives. Proc Natl Acad Sci U S A. 2009; 106(38):16096-101. PMC: 2752511. DOI: 10.1073/pnas.0908248106. View

18.

Yi W, Liu X, Li Y, Li J, Xia C, Zhou G . Remodeling bacterial polysaccharides by metabolic pathway engineering. Proc Natl Acad Sci U S A. 2009; 106(11):4207-12. PMC: 2657399. DOI: 10.1073/pnas.0812432106. View

19.

Chen Y, Thon V, Li Y, Yu H, Ding L, Lau K . One-pot three-enzyme synthesis of UDP-GlcNAc derivatives. Chem Commun (Camb). 2011; 47(38):10815-7. PMC: 11279325. DOI: 10.1039/c1cc14034e. View

20.

Thibodeaux C, Melancon 3rd C, Liu H . Natural-product sugar biosynthesis and enzymatic glycodiversification. Angew Chem Int Ed Engl. 2008; 47(51):9814-59. PMC: 2796923. DOI: 10.1002/anie.200801204. View