Enzymatic synthesis of L-norephedrine by coupling recombinant pyruvate decarboxylase and ω-transaminase

Applied Microbiology and Biotechnology

Volumn 98, Issue 17, 2014, Pages 7399-7408

  Wu, Xuri ^a   Fei, Mengdan ^a   Chen, Yong ^a   Wang, Zongqiang ^a   Chen, Yijun ^a  

^a CHINA PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

Biosynthesis; l Norephedrine; l Phenylacetylcarbinol; Pyruvate decarboxylase; Transaminase

Indexed keywords

AGRICULTURAL CHEMICALS; BIOCHEMISTRY; DRUG PRODUCTS; YEAST;

ASYMMETRIC SYNTHESIS; EFFICIENT SYNTHESIS; ENZYMATIC SYNTHESIS; L-NOREPHEDRINE; OPTICALLY PURE COMPOUNDS; PHENYLACETYLCARBINOL; PYRUVATE DECARBOXYLASE; SYSTEMATIC OPTIMIZATION;

BIOSYNTHESIS;

AMINOTRANSFERASE; EPHEDRINE; NOREPHEDRINE; OMEGA TRANSAMINASE; PYRUVATE DECARBOXYLASE; RECOMBINANT ENZYME; UNCLASSIFIED DRUG; PHENYLPROPANOLAMINE;

ALCOHOL; ALKALOID; CATALYSIS; ENZYME ACTIVITY; OPTIMIZATION; REACTION KINETICS;

ARTICLE; ASYMMETRIC SYNTHESIS; BIOCATALYSIS; BIOCATALYST; DRUG SYNTHESIS; NONHUMAN; NUCLEOTIDE SEQUENCE; QUANTUM YIELD; REACTION OPTIMIZATION; SACCHAROMYCES CEREVISIAE; STEREOCHEMISTRY; VIBRIO FLUVIALIS; ENZYMOLOGY; METABOLISM; VIBRIO;

SACCHAROMYCES CEREVISIAE; VIBRIO FLUVIALIS;

PHENYLPROPANOLAMINE; PYRUVATE DECARBOXYLASE; SACCHAROMYCES CEREVISIAE; TRANSAMINASES; VIBRIO;

EID: 84906951235     PISSN: 01757598     EISSN: 14320614     Source Type: Journal    
DOI: 10.1007/s00253-014-5797-1     Document Type: Article

References (36)

1. Abrahamson MJ, Vázquez-Figueroa E, Woodall NB, Moore JC, Bommarius AS (2012) Development of an amine dehydrogenase for synthesis of chiral amines. Angew Chem Int Ed 51:3969-3972
2. Bergmeie SC (2000) The synthesis of vicinal amino alcohols. Tetrahedron 56:2561-2576
3. Bornscheuer UT, Huisman GW, Kazlauskas RJ, Lutz S, Moore JC, Robins K (2012) Engineering the third wave of biocatalysis. Nature 485:185-194
4. Clifton JE, Collins I, Hallett P (1982) Arylethanolamines derived from salicylamide with α- and β-adrenoceptor blocking activities. Preparation of labetalol, its enantiomers and related salicylamides. J Med Chem 25:670-679 (Pubitemid 13238102)
5. France S, Guerin DJ, Miller SJ, Lectka T (2003) Nucleophilic chiral amines as catalysts in asymmetric synthesis. Chem Rev 103:2985-3012
6. Ingram CU, Bommer M, Smith MEB, Dalby PA, Ward JM, Hailes HC, Lye GJ (2006) One-pot synthesis of amino-alcohols using a de-novo transketolase and beta-alanine: pyruvate transaminase pathway in Escherichia coli. Biotechnol Bioeng 96:559-569 (Pubitemid 46232361)
7. Kasat RB, Linda Wang NH, Franses EI (2008) Experimental probing and modeling of key sorbent-solute interactions of norephedrine enantiomers with polysaccharide-based chiral stationary phases. J Chromatogr A 1190:110-119
8. Kim PY, Pollard DJ, Woodley JM (2007) Substrate supply for effective biocatalysis. Biotechnol Prog 23:74-82 (Pubitemid 46293490)
9. Koszelewski D, Tauber K, Faber K, Kroutil W (2010) ω-Transaminases for the synthesis of non-racemic alpha-chiral primary amines. Trends Biotechnol 28:324-332
10. Kreutz OC,Moran PJS, Rodrigues JAR (1997) Baker's yeast reduction of (E)-l-phenyl-l, 2-propanedione 2-(o-methyloxime). A key step for a (-)- norephedrine synthesis. Tetrahedron Asymmetry 8:2649-2653 (Pubitemid 27356960)
11. Krizevski R, Dudai N, Bar E, Lewinsohn E (2007) Developmental patterns of phenylpropylamino alkaloids accumulation in khat (Catha edulis, Forsk). J Ethnopharmacol 114:432-438 (Pubitemid 350026227)
12. Lee HK, Kang S, Choi EB (2012) Stereoselective synthesis of norephedrine and norpseudoephedrine by using asymmetric transfer hydrogenation accompanied by dynamic kinetic resolution. J Org Chem 77:5454-5460
13. Liu M, Sergienko EA, Guo F, Wang J, Tittmann K, Hubner G, Furey W, Jordan F (2001) Catalytic acid-base groups in yeast pyruvate decarboxylase. 1. Site-directed mutagenesis and steady-state kinetic studies on the enzyme with the D28A, H114F, H115F, and E477Q substitutions. Biochemistry 40:7355-7368 (Pubitemid 32578001)
14. Liu TL,Wang CJ, Zhang XM (2013) Synthesis of chiral aliphatic amines through asymmetric hydrogenation. Angew Chem Int Ed 52:8416-8419
15. Luna A, Alfonso I, Gotor V (2002) Biocatalytic approaches toward the synthesis of both enantiomers of trans-cyclopentane-1,2-diamine. Org Lett 4:3627-3629
16. Mahmoud WM, El-Sayed AH, Coughlin RW (1990) Effect of beta-cyclodextrin on production of L-phenylacetylcarbinol by immobilized cells of Saccharomyces cerevisiae. Biotechnol Bioeng 36:256-262 (Pubitemid 20283259)
17. Purkarthofer T, Gruber K, Gruber-Khadjawi M, Waich K, Skranc W, Mink D, Griengl H (2006) A biocatalytic henry reaction - the hydroxynitrile lyase from Hevea brasiliensis also catalyzes nitroaldol reactions. Angew Chem Int Ed 45:3454-3456 (Pubitemid 44098954)
18. Rogers PL, Shin HS, Wang B (1997) Biotransformation for L-ephedrine production. Adv Biochem Eng Biotechnol 56:33-59
19. Sandford V, Breuer M, Hauer B, Rogers P, Rosche B (2005) (R)-phenylacetylcarbinol production in aqueous/organic two-phase systems using partially purified pyruvate decarboxylase from Candida utilis. Biotechnol Bioeng 91:190-198 (Pubitemid 41158946)
20. Satianegara G, Breuer M, Hauer B, Rogers PL, Rosche B (2006) Enzymatic (R)-phenylacetylcarbinol production in a benzaldehyde emulsion system with Candida utilis cells. Appl Microbiol Biotechnol 70:170-175
21. Savile CK, Janey JM, Mundorff EC, Moore JC, Tam S, Jarvis WR, Colbeck JC, Krebber A, Fleitz FJ, Brands J, Devine PN, Huisman GW, Hughes GJ (2010) Biocatalytic asymmetric synthesis of chiral amines from ketones applied to sitagliptin manufacture. Science 329:305-309
22. Schmid A, Dordick JS, Hauer B, Kiener A, Wubbolts M, Witholt B (2001) Industrial biocatalysis today and tomorrow. Nature 409:258-268 (Pubitemid 32144296)
23. Schoemaker HE, Mink D, Wubbolts MG (2004) Dispelling the myths - biocatalysis in industrial synthesis. Science 299:1694-1697
24. Seo JH, Kyung D, Joo K, Lee J, Kim BG (2011) Necessary and sufficient conditions for the asymmetric synthesis of chiral amines using ω-aminotransferases. Biotechnol Bioeng 108:253-263
25. Shin JS, Kim BG (1998) Kinetic modeling of omega-transamination for enzymatic kinetic resolution of alpha-methylbenzylamine. Biotechnol Bioeng 60:534-540
26. Shin JS, Kim BG (1999) Asymmetric synthesis of chiral amines with ω-transaminase. Biotechnol Bioeng 65:206-211
27. Shin JS, Kim BG (2002) Substrate inhibition mode of ω-transaminase from Vibrio fluvialis JS17 is dependent on the chirality of substrate. Biotechnol Bioeng 77:832-837
28. Shin JS, Kim BG (2009) Transaminase-catalyzed asymmetric synthesis of L-2-aminobutyric acid from achiral reactants. Biotechnol Lett 31:1595-1599
29. Shin HS, Rogers PL (1996) Production of L-phenylacetylcarbinol (L-PAC) from benzaldehyde using partially purified pyruvate decarboxylase (PDC). Biotechnol Bioeng 49:52 -62
30. Shin JS, Yun H, Jang JW, Park I, Kim BG (2003) Purification, characterization, and molecular cloning of a novel amine: pyruvate transaminase from Vibrio fluvialis JS17. Appl Microbiol Biotechnol 61:463-471 (Pubitemid 36751008)
31. Thiel OR, Bernard C, Tormos W, Brewin A, Hirotani S, Murakami K, Saito K, Larsen RD, Martinelli MJ, Reider PJ (2008) Practical synthesis of the calcimimetic agent, cinacalcet. Tetrahedron Lett 49:13-15 (Pubitemid 350191895)
32. Wellman PJ (1990) A review of the physiological bases of the anorexic action of phenylpropanolamine (l-norephedrine). Neurosci Behav Rev 14:339-355
33. Xu GC, Yu HL, Zhang XY, Xu JH (2012) Access to optically active aryl halohydrins using a substrate-tolerant carbonyl reductase discovered from Kluyveromyces thermotolerans. ACS Catal 2:2566-2571
34. Youshko MI, van Rantwijk F, Sheldon RA (2001) Enantioselective acylation of chiral amines catalysed by aminoacylase I. Tetrahedron Asymmetry 12:3267-3271 (Pubitemid 34159168)
35. Zhang JL, Zhu TY, Wu XR, Chen YJ (2013) Enhancement of biocatalytic efficiency by increasing substrate loading: enzymatic preparation of L-homophenylalanine. Appl Microbiol Biotechnol 97:8487-8494
36. Zhang JL, Tao SS, Zhang BJ, Wu XR, Chen YJ (2014) Microparticle-based strategy for controlled release of substrate for the biocatalytic preparation of L-homophenylalanine. ACS Catal 4:1584-1587