Identification of homophenylalanine biosynthetic genes from the cyanobacterium Nostoc punctiforme PCC73102 and application to its microbial production by Escherichia coli

Applied and Environmental Microbiology

Volumn 79, Issue 7, 2013, Pages 2201-2208

  Koketsu, Kento ^a   Mitsuhashi, Satoshi ^a   Tabata, Kazuhiko ^a  

^a KYOWA HAKKO BIO CO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANGIOTENSIN-CONVERTING ENZYME; BIOINFORMATICS ANALYSIS; CHEMOENZYMATIC ROUTE; CHIRAL BUILDING BLOCKS; FERMENTATIVE PRODUCTION; MICROBIAL PRODUCTION; PROTEASOME INHIBITORS; SUBSTRATE SPECIFICITY;

AMINO ACIDS; BACTERIA; BIOCHEMISTRY; BIOINFORMATICS; BIOSYNTHESIS; ENZYME ACTIVITY; ESCHERICHIA COLI; GENES; STRAIN;

SUBSTRATES;

2 AMINO 4 PHENYLBUTYRIC ACID; 2-AMINO-4-PHENYLBUTYRIC ACID; AMINOBUTYRIC ACID DERIVATIVE;

AMINO ACID; BIOINFORMATICS; BIOLOGICAL PRODUCTION; BIOTECHNOLOGY; COLIFORM BACTERIUM; CYANOBACTERIUM; DRUG; GENE EXPRESSION; HYPOTHESIS TESTING; INHIBITOR; MICROBIAL ACTIVITY; PHENOLIC COMPOUND; SUBSTRATE; TOLERANCE;

ARTICLE; BIOLOGY; BIOSYNTHESIS; BIOTECHNOLOGY; ESCHERICHIA COLI; GENETICS; METABOLIC ENGINEERING; METABOLISM; METHODOLOGY; MULTIGENE FAMILY; NOSTOC;

AMINOBUTYRATES; BIOSYNTHETIC PATHWAYS; BIOTECHNOLOGY; COMPUTATIONAL BIOLOGY; ESCHERICHIA COLI; METABOLIC ENGINEERING; MULTIGENE FAMILY; NOSTOC;

ESCHERICHIA COLI; NOSTOC PUNCTIFORME; NOSTOC SP.;

EID: 84876161680     PISSN: 00992240     EISSN: 10985336     Source Type: Journal    
DOI: 10.1128/AEM.03596-12     Document Type: Article

References (37)

1. Brown NJ, Vaughan DE. 1998. Angiotensin-converting enzyme inhibitors. Circulation 97:1411-1420.
2. Kuhn DJ, Chen Q, Voorhees PM, Strader JS, Shenk KD, Sun CM, Demo SD, Bennett MK, van Leeuwen FWB, Chanan-Khan AA, Orlowski RZ. 2007. Potent activity of carfilzomib, a novel, irreversible inhibitor of the ubiquitin-proteasome pathway, against preclinical models of multiple myeloma. Blood 110:3281-3290.
3. Ahmad AL, Oh PC, Shukor SRA. 2009. Sustainable biocatalytic synthesis of L-homophenylalanine as pharmaceutical drug precursor. Biotechnol. Adv. 27:286-296.
4. Asano Y, Yamada A, Kato Y, Yamaguchi K, Hibino Y, Hirai K, Kondo K. 1990. Enantioselective synthesis of (S)-amino acids by phenylalanine dehydrogenase from Bacillus sphaericus: use of natural and recombinant enzymes. J. Org. Chem. 55:5567-5571.
5. Chen ST, Tseng MJ, Kao T, Sookkheo B, Surat T. November 2000. Facile synthesis of L-homophenylalanine by equilibrium shift enzymatic reaction using engineered tyrosine aminotransferase. US patent 6,146,859.
6. Kao CH, Lo HH, Hsu SK, Hsu WH. 2008. A novel hydantoinase process using recombinant Escherichia coli cells with dihydropyrimidinase, and L-N-carbamoylase activities as biocatalyst for the production of Lhomophenylalanine. J. Biotechnol. 134:231-239.
7. Dawson GW, Hick AJ, Bennett RN, Donald A, Pickett JA, Wallsgrove RM. 1993. Synthesis of glucosinolate precursors and investigations into the biosynthesis of phenylalkyl- and methylthioalkylglucosinolate. J. Biol. Chem. 268:27154-27159.
8. Tan LT. 2007. Bioactive natural products from marine cyanobacteria for drug discovery. Phytochemistry 68:954-979.
9. Underhill EW. 1967. Biosynthesis of mustard oil glucosides: 3-benzylmalic acid, a precursor of 2-amino-4-phenylbutyric acid and of gluconasturtiin. Can. J. Biochem. 46:401-406.
10. Rouhiainen L, Jokela J, Fewer DP, Urmann M, Sivonen K. 2010. Two alternative starter modules for the non-ribosomal biosynthesis of specific anabaenopeptin variants in anabaena (cyanobacteria). Chem. Biol. 17: 265-273.
11. Finking R, Marahiel MA. 2004. Biosynthesis of nonribosomal peptides. Annu. Rev. Microbiol. 58:453-488.
12. Bachmann BJ. 1987. Derivations and genotypes of some mutant derivatives of Escherichia coli K-12, p 1191-1219. In Ingraham JL, Low KB, Magasanik B, Schaechter M, Umbarger HE (ed), Escherichia coli and Salmonella typhimurium: cellular and molecular biology. American Society for Microbiology, Washington, DC.
13. Nelms J, Gonzalez DH, Yoshida T, Fotheringham I. 1992. Novel mutation in the pheA gene of Escherichia coli K-12 which result in highly feedback inhibition-resistant variants of chorismate mutase/prephenate dehydratase. Appl. Environ. Microbiol. 58:2592-2598.
14. Kikuchi Y, Tsujimoto K, Kurahashi O. 1997. Mutational analysis of the feedback sites of phenylalanine-sensitive 3-deoxy-D-arabinoheptulosonate- 7-phosphate synthase of Escherichia coli. Appl. Environ. Microbiol. 63:761-762.
15. Baba T, Ara T, Hasegawa M, Takai Y, Okumura Y, Baba M, Datsenko KA, Tomita M, Wanner BL, Mori H. 2006. Construction of Escherichia coli K-12 in-frame, single-gene knockout mutants: the Keio collection. Mol. Syst. Biol. 2:2006.0008. doi:10.1038/msb4100050.
16. Sambrook J, Russell DW. 2001. Molecular cloning: a laboratory manual, 3rd ed. Cold Spring Harbor Laboratory Press, Plainview, NY.
17. Felnagle EA, Chaubey A, Noey EL, Houk KN, Liao JC. 2012. Engineering synthetic recursive pathways to generate non-natural small molecules. Nat. Chem. Biol. 8:518-526.
18. Meeks JC, Elhai J, Thiel T, Potts M, Larimer F, Lamerdin J, Predki Atlas PR. 2001. An overview of the genome of Nostoc punctiforme, a multicellular, symbiotic cyanobacterium. Photosynth. Res. 70:85-106.
19. Altschul SF, Gish W, Miller W, Myers EW, Lipman DJ. 1990. Basic local alignment search tool. J. Mol. Biol. 215:403-410.
20. Larkin MA, Blackshields G, Brown NP, Chenna R, McGettigan PA, McWilliam H, Valentin F, Wallace IM, Wilm A, Lopez R, Thompson JD, Gibson TJ, Higgins DG. 2007. Clustal W and Clustal X version 2.0. Bioinfomatics 23:2947-2948.
21. de Carvalho LPS. Frantom PA, Argyrou A, Blanchard JS. 2009. Kinetic evidence for interdomain communication in the allosteric regulation of R-isopropylmalate synthase from Mycobacterium tuberculosis. Biochemistry 48:1996-2004.
22. Manikandan K, Geerlof A, Zozulya AV, Svergun DI, Weiss MS. 2011. Structural studies on the enzyme complex isopropylmalate isomerase (LeuCD) from Mycobacterium tuberculosis. Proteins 79:35-49.
23. Keasling JD. 2008. Synthetic biology for synthetic chemistry. ACS Chem. Biol. 3:64-76.
24. Collier RH, Kohlhaw G. 1972. Nonidentity of the aspartate and the aromatic aminotransferase components of transaminase A in Escherichia coli. J. Bacteriol. 112:365-372.
25. Powell JT, Morrison JF. 1978. The purification and properties of the aspartate aminotransferase and aromatic-amino-acid aminotransferase from Escherichia coli. Eur. J. Biochem. 87:391-400.
26. Méjean A, Mazmouz R, Mann S, Calteau A, Médigue C, Ploux O. 2010. The genome sequence of the cyanobacterium Oscillatoria sp. PCC 6506 reveals several gene clusters responsible for the biosynthesis of toxins and secondary metabolites. J. Bacteriol. 192:5264-5265.
27. Fewer DP, Jokela J, Rouhiainen L, Wahlsten M, Koskenniemi K, Stal LJ, Sivonen K. 2009. The non-ribosomal assembly and frequent occurrence of the protease inhibitors spumigins in the bloom-forming cyanobacterium Nodularia spumigena. Mol. Microbiol. 73:924-937.
28. Cacho RA, Jiang W, Chooi Y-H, Walsh CT, Tang Y. 2012. Identification and characterization of the echinocandin B biosynthetic gene cluster from Emericella ruglosa NRRL11440. J. Am. Chem. Soc. 134:16781-16790.
29. Plaza A, Bewley CA. 2006. Largamides A-H, unusual cyclic peptides from the marine cyanobacterium Oscillatoria sp. J. Org. Chem. 71:6898-6907.
30. Falk FL, Vogel C, Textor S, Bartram S, Hick A, Pickett JA, Gershenzon J. 2004. Glucosinolate biosynthesis: demonstration and characterization of the condensing enzyme of the chain elongation cycle in Eruca sativa. Phytochemistry 65:1073-1084.
31. Knill T, Reichelt M, Paetz C, Gershenzon J, Binder S. 2009. Arabidopsis thaliana encodes a bacterial-type heterodimeric isopropylmalate isomerase involved in both Leu biosynthesis and the Met chain elongation pathway of glucosinolate formation. Plant Mol. Biol. 71:227-239.
32. Marcheschi RJ, Li H, Zhang K, Noey EL, Kim S, Chaubey A, Houk KN, Liao JC. 2012. A synthetic recursive "+1" pathway for carbon chain elongation. ACS Chem. Biol. 7:689-697.
33. Py B, Barras F. 2010. Building Fe-S proteins: bacterial strategies. Nat. Rev. Microbiol. 8:436-446.
34. Fontecave Ollagnier de Choudens MS. 2008. Iron-sulfur cluster biosynthesis in bacteria: mechanisms of cluster assembly and transfer. Arch. Biochem. Biophys. 474:226-237.
35. Ajikumar PK, Xiao W-H, Tyo KEJ, Wang Y, Simeon F, Leonard E, Mucha O, Phon TH, Pfeifer B, Stephanopoulos G. 2010. Isoprenoid pathway optimization for taxol precursor overproduction in Escherichia coli. Science 330:70-74.
36. Galkin A, Kulakova L, Yoshimura T, Soda K, Esaki N. 1997. Synthesis of optically active amino acids from α-keto acids with Escherichia coli cells expressing heterologous genes. Appl. Environ. Microbiol. 63:4651-4656.
37. Koma D, Yamanaka H, Moriyoshi K, Ohmoto T, Sakai K. 2012. Production of aromatic compounds by metabolically engineered Escherichia coli with an expanded shikimate pathway. Appl. Environ. Microbiol. 78:6203-6216.