Enzymatic formation of a resorcylic acid by creating a structure-guided single-point mutation in stilbene synthase

Protein Science

Volumn 24, Issue 2, 2015, Pages 167-173

  Bhan, Namita ^a   Li, Lingyun ^a   Cai, Chao ^a   Xu, Peng ^a   Linhardt, Robert J ^a,b   Koffas, Mattheos A G ^a,b  

^a RENSSELAER POLYTECHNIC INSTITUTE   (United States)

^b Rensselaer Polytechnic Institute   (United States)

Author keywords

novel non natural polyphenols; resorcylic acid; stilbene synthase; structure guided mutants; type III polyketides synthases

Indexed keywords

CHALCONE SYNTHASE; MALONYL COENZYME A; POLYKETIDE SYNTHASE; STILBENE SYNTHASE; SYNTHETASE; THREONINE; UNCLASSIFIED DRUG; ACYLTRANSFERASE; ALPHA-RESORCYLIC ACID; HYDROXYBENZOIC ACID DERIVATIVE; RESORCINOL DERIVATIVE;

ALDOL REACTION; AMINO ACID SUBSTITUTION; AROMATIZATION; ARTICLE; CLAISEN CONDENSATION; CRYSTAL STRUCTURE; CYCLIZATION; DECARBOXYLATION; GRAPE; HYDROGEN BOND; HYDROLYSIS; NONHUMAN; POINT MUTATION; PRIORITY JOURNAL; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; TANDEM MASS SPECTROMETRY; CHEMICAL STRUCTURE; CHEMISTRY; ENZYMOLOGY; ESCHERICHIA COLI; GENE EXPRESSION; GENETICS; METABOLISM; SITE DIRECTED MUTAGENESIS; VITIS;

VITIS VINIFERA;

ACYLTRANSFERASES; ESCHERICHIA COLI; GENE EXPRESSION; HYDROXYBENZOATES; MODELS, MOLECULAR; MUTAGENESIS, SITE-DIRECTED; POINT MUTATION; RESORCINOLS; VITIS;

EID: 84928898037     PISSN: 09618368     EISSN: 1469896X     Source Type: Journal    
DOI: 10.1002/pro.2600     Document Type: Article

References (24)

1. Funa N, Ohnishi Y, Fujii I, Shibuya M, Ebizuka Y, Horinouchi S, (1999) A new pathway for polyketide synthesis in microorganisms. Nature 400: 897-899.
2. Katsuyama Y, Ohnishi Y, Type III polyketide synthases in microorganisms. In:, Hopwood DA, Ed. (2012) Natural product biosynthesis by microorganisms and plant, Part A, Vol. 515: Methods in enzymology. San Diego: Elsevier Academic Press, pp 359-377.
3. Yu DY, Xu FC, Zeng J, Zhan JX, (2003) Type III polyketide synthases in natural product biosynthesis. Iubmb Life 64: 285-295.
4. Austin MB, Noel AJP, (2003) The chalcone synthase superfamily of type III polyketide synthases. Nat Prod Rep 20: 79-110.
5. Abe I, (2012) Novel applications of plant polyketide synthases. Curr Opin Chem Biol 16: 179-185.
6. Austin MB, Bowman ME, Ferrer JL, Schroder J, Noel JP, (2004) An aldol switch discovered in stilbene synthases mediates cyclization specificity of type III polyketide synthases. Chem Biol 11: 1179-1194.
7. Hrazdina G, Kreuzaler F, Hahlbrock K, Grisebach H, (1976) Substrate specificity of flavanone synthase from cell suspension cultures of parsley and structure of release products in vitro. Arch Biochem Biophys 175: 392-399.
8. Abe I, (2008) Engineering of plant polyketide biosynthesis. Chem Pharm Bull 56: 1505-1514.
9. Abe I, (2009) Engineered biosynthesis of plant polyketides: structure-based and precursor-directed approach. Top Curr Chem 297: 45-66.
10. Morita H, Yamashita M, Shi S-P, Wakimoto T, Kondo S, Kato R, Sugio S, Kohno T, Abe I, (2011) Synthesis of unnatural alkaloid scaffolds by exploiting plant polyketide synthase. Proc Natl Acad Sci USA 108: 13504-13509.
11. Chemler JA, Lim CG, Daiss JL, Koffas MA, (2010) A versatile microbial system for biosynthesis of novel polyphenols with altered estrogen receptor binding activity. Chem Biol 17: 392-401.
12. Chemler JA, Koffas MAG, (2008) Metabolic engineering for plant natural product biosynthesis in microbes. Curr Opin Biotech 19: 597-605.
13. Bhan N, Xu P, Koffas MAG, (2013) Pathway and protein engineering approaches to produce novel and commodity small molecules. Curr Opin Biotech 24: 1137-1143.
14. Tautenhahn R, Bottcher C, Neumann S, (2008) Highly sensitive feature detection for high resolution LC/MS. BMC Bioinform 9: 504.
15. Smith CA, Want EJ, O'Maille G, Abagyan R, Siuzdak G, (2006) XCMS: processing mass spectrometry data for metabolite profiling using Nonlinear peak alignment, matching, and identification. Anal Chem 78: 779-787.
16. Eckermann C, Schroder G, Eckermann S, Strack D, Schmidt E, Schneider B, Schroder J, (2003) Stilbenecarboxylate biosynthesis: a new function in the family of chalcone synthase-related proteins. Phytochem 62: 271-286.
17. Funa N, Awakawa T, Horinouchi S, (2007) Pentaketide resorcylic acid synthesis by type III polyketide synthase from Neurospora crassa. J Biol Chem 282: 14476-14481.
18. Gorham J, The stilbenoids. In:, Harbome JBST, Reinhold L, Ed. (1980) Oxford: Pergamon Press 203-252.
19. Hirano K, Sakai S, Ishikawa T, Avci FY, Linhardt RJ, Toida T, (2005) Preparation of the methyl ester of hyaluronan and its enzymatic degradation. Carb Res 340: 2297-2304.
20. Stockigt J, Zenk MH, (1975) Chemical syntheses and properties of hydroxycinnamoyl coenzyme A derivative. Z Naturforschung 30: 352-358.
21. Tautenhahn R, Patti GJ, Rinehart D, Siuzdak G, (2012) XCMS online: a web-based platform to process untargeted metabolomic data. Anal Chem 84: 5035-5039.
22. Guex N, Peitsch MC, (1997) SWISS-MODEL and the Swiss-PdbViewer: an environment for comparative protein modeling. Electrophoresis 18: 2714-2723.
23. Liang J, Edelsbrunner H, Woodward C, (1998) Anatomy of protein pockets and cavities: measurement of binding site geometry and implications for ligand design. Protein Sci 7: 1884-1897.
24. Liang J, Edelsbrunner H, Woodward C, (1998) Anatomy of protein pockets and cavities: measurement of binding site geometry and implications for ligand design. Protein Sci 7: 1884-1897.