In vitro evidence of chain transfer to tetraethylene glycols in enzymatic polymerization of polyhydroxyalkanoate

Applied Microbiology and Biotechnology

Volumn 97, Issue 11, 2013, Pages 4821-4829

  Tomizawa, Satoshi ^a,d   Sato, Shun ^b   Lan, John Chi Wei ^c   Nakamura, Yoshiyuki ^a   Abe, Hideki ^a,d   Tsuge, Takeharu ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

^c YUAN ZE UNIVERSITY   (Taiwan)

^d RIKEN   (Japan)

Author keywords

Chain transfer reaction; Enoyl CoA hydratase; Ethylene glycol derivatives; In vitro polymerization; PHA synthase; Polyhydroxyalkanoate

Indexed keywords

CHAIN-TRANSFER REACTIONS; GLYCOL DERIVATIVES; HYDRATASE; IN-VITRO; PHA SYNTHASES; POLY-HYDROXYALKANOATE;

ETHYLENE GLYCOL; POLYMERIZATION;

SYNTHESIS (CHEMICAL);

BUTYROLACTONE; ENOYL COENZYME A HYDRATASE; ETHYLENE GLYCOL DERIVATIVE; POLYHYDROXYALKANOIC ACID; TETRAETHYLENE GLYCOL; UNCLASSIFIED DRUG;

ENZYME; ENZYME ACTIVITY; ETHYLENE; NUCLEAR MAGNETIC RESONANCE; POLYMERIZATION;

AEROMONAS PUNCTATA; ARTICLE; DELFTIA ACIDOVORANS; ENANTIOSELECTIVITY; EPIMERIZATION; IN VITRO STUDY; MOLECULAR MIMICRY; MOLECULAR WEIGHT; NONHUMAN; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; PSEUDOMONAS PUTIDA; STRUCTURE ANALYSIS; TRANSESTERIFICATION;

ACYLTRANSFERASES; AEROMONAS CAVIAE; DELFTIA ACIDOVORANS; ENOYL-COA HYDRATASE; POLYETHYLENE GLYCOLS; POLYHYDROXYALKANOATES; POLYMERIZATION; PSEUDOMONAS PUTIDA;

AEROMONAS PUNCTATA; DELFTIA ACIDOVORANS; PSEUDOMONAS PUTIDA;

EID: 84878015695     PISSN: 01757598     EISSN: 14320614     Source Type: Journal    
DOI: 10.1007/s00253-013-4798-9     Document Type: Article

References (33)

1. Agus J, Kahar P, Abe H, Doi Y, Tsuge T (2006) Molecular weight characterization of poly[(R)-3-hydroxybutyrate] synthesized by genetically engineered strains of Escherichia coli. Polym Degrad Stab 91:1138-1146
2. Ashby R, Shi FY, Gross RA (1997) Use of poly(ethylene glycol) to control the end group structure and molecular weight of poly(3-hydroxybutyrate) formed by Alcaligenes latus DSM 1122. Tetrahedron 53:15209-15223
3. Fong JC, Schulz H (1981) Short-chain and long-chain enoyl-CoA hydratases from pig heart muscle. Methods Enzymol 71:390-398
4. Foster LJ (2007) Biosynthesis, properties and potential of natural-synthetic hybrids of polyhydroxyalkanoates and polyethylene glycols. Appl Microbiol Biotechnol 75:1241-1247
5. Fukui T, Shiomi N, Doi Y (1998) Expression and characterization of (R)-specific enoyl coenzyme A hydratase involved in polyhydroxyalkanoate biosynthesis by Aeromonas caviae. J Bacteriol 180:667-673
6. Gerngross TU, Martin DP (1995) Enzyme-catalyzed synthesis of poly[(R)-(-)-3-hydroxybutyrate]: formation of macroscopic granules in vitro. Proc Natl Acad Sci U S A 92:6279-6283
7. Kawaguchi Y, Doi Y (1990) Structure of native poly(3-hydroxybutyrate) granules characterized by X-ray diffraction. FEMS Microbiol Lett 70:151-155
8. Kawaguchi Y, Doi Y (1992) Kinetics and mechanism of synthesis and degradation of poly(3-hydroxybutyrate) in Alcaligenes eutrophus. Macromolecules 25:2324-2329
9. King MT, Reiss PD (1985) Separation and measurement of short-chain coenzyme-A compounds in rat liver by reversed-phase high-performance liquid chromatography. Anal Biochem 146:173-179
10. King MT, Reiss PD, Cornell NW (1988) Determination of short-chain coenzyme A compounds by reversed-phase high-performance liquid chromatography. Methods Enzymol 166:70-79
11. Lawrence AG, Choi J, Rha C, Stubbe J, Sinskey AJ (2005) In vitro analysis of the chain termination reaction in the synthesis of poly-(R)-β- hydroxybutyrate by the class III synthase from Allochromatium vinosum. Biomacromolecules 6:2113-2119
12. Lenz RW, Farcet C, Dijkstra PJ, Goodwin S, Zhang S (1999) Extracellular polymerization of 3-hydroxyalkanoate monomers with the polymerase of Alcaligenes eutrophus. Int J Biol Macromol 25:55-60
13. Madden LA, Anderson AJ, Shah DT, Asrar J (1999) Chain termination in polyhydroxyalkanoate synthesis: involvement of exogenous hydroxy-compounds as chain transfer agents. Int J Biol Macromol 25:43-53
14. Moskowitz GJ, Merrick JM (1969) Metabolism of poly-β- hydroxybutyrate. II. Enzymic synthesis of d-(-)-β-hydroxybutyryl coenzyme A by an enoyl hydrase from Rhodospirillum rubrum. Biochemistry 8:2748-2755
15. Nelson KE, Weinel C, Paulsen IT, Dodson RJ, Hilbert H, Martins dos Santos VAP, Fouts DE, Gill SR, Pop M, Holmes M, Brinkac L, Pop M, Holmes M, Brinkac L, Beanan M, DeBoy RT, Daugherty S, Kolonay J, Madupu R, Nelson W, White O, Peterson J, Khouri H, Hance I, Chris Lee P, Holtzapple E, Scanlan D, Tran K, Moazzez A, Utterback T, Rizzo M, Lee K, Kosack D, Moestl D, Wedler H, Lauber J, Stjepandic D, Hoheisel J, Straetz M, Heim S, Kiewitz C, Eisen J, Timmis KN, Düsterhöft A, Tümmler B, Fraser CM (2002) Complete genome sequence and comparative analysis of the metabolically versatile Pseudomonas putida KT2440. Environ Microbiol 4:799-808
16. Normi YM, Hiraishi T, Taguchi S, Abe H, Sudesh K, Najimudin N, Doi Y (2005) Characterization and properties of G4X mutants of Ralstonia eutropha PHA synthase for poly(3-hydroxybutyrate) biosynthesis in Escherichia coli. Macromol Biosci 5:197-206
17. Olson AR, Miller RJ (1938) The mechanism of the aqueous hydrolysis of β-butyrolactone. J Am Chem Soc 60:2687-2692
18. Sanguanchaipaiwong V, Gabelish CL, Hook J, Scholz C, Foster LJR (2004) Biosynthesis of natural-synthetic hybrid copolymers: polyhydroxyoctanoate- diethylene glycol. Biomacromolecules 5:643-649
19. Sato S, Nomura CT, Abe H, Doi Y, Tsuge T (2007) Poly[(R)-3- hydroxybutyrate] formation in Escherichia coli from glucose through an enoyl-CoA hydratase-mediated pathway. J Biosci Bioeng 103:38-44
20. Sato S, Ono Y, Mochiyama Y, Sivaniah E, Kikkawa Y, Sudesh K, Hiraishi T, Doi Y, Abe H, Tsuge T (2008) Polyhydroxyalkanoate film formation and synthase activity during in vitro and in situ polymerization on hydrophobic surfaces. Biomacromolecules 9:2811-2818
21. Shi F, Ashby R, Gross RA (1996a) Use of poly(ethylene glycol)s to regulate poly(3-hydroxybutyrate) molecular weight during Alcaligenes eutrophus cultivations. Macromolecules 29:7753-7758
22. Shi F, Gross RA, Rutherford DR (1996b) Microbial polyester synthesis: effects of poly(ethylene glycol) on product composition, repeat unit sequence, and end group structure. Macromolecules 29:10-17
23. Simon EJ, Shemin D (1953) The preparation of S-succinyl coenzyme A. J Am Chem Soc 75:2520
24. Song JJ, Zhang S, Lenz RW, Goodwin S (2000) In vitro polymerization and copolymerization of 3-hydroxypropionyl-CoA with the PHB synthase from Ralstonia eutropha. Biomacromolecules 1:433-439
25. Stubbe J, Tian J (2003) Polyhydroxyalkanoate (PHA) homeostasis: the role of the PHA synthase. Nat Prod Rep 20:445-457
26. Sudesh K, Fukui T, Doi Y (1998) Genetic analysis of Comamonas acidovorans polyhydroxyalkanoate synthase and factors affecting the incorporation of 4-hydroxybutyrate monomer. Appl Environ Microbiol 64:3437-3443
27. Sudesh K, Abe H, Doi Y (2000) Synthesis, structure and properties of polyhydroxyalkanoates: biological polyesters. Prog Polym Sci 25:1503-1555
28. Tajima K, Satoh Y, Nakazawa K, Tannai H, Erata T, Munekata M, Kamachi M, Lenz RW (2004) Chemoenzymatic synthesis of poly(3-hydroxybutyrate) in a water-organic solvent two-phase system. Macromolecules 37:4544-4546
29. Tomizawa S, Saito Y, Hyakutake M, Nakamura Y, Abe H, Tsuge T (2010) Chain transfer reaction catalyzed by various polyhydroxyalkanoate synthases with poly(ethylene glycol) as an exogenous chain transfer agent. Appl Microbiol Biotechnol 87:1427-1435
30. Tomizawa S, Yoshioka M, Ushimaru K, Tsuge T (2012) Preparative synthesis of poly[(R)-3-hydroxybutyrate] monomer for enzymatic cell-free polymerization. Polym J 44:982-985
31. Tsuge T, Imazu S, Takase K, Taguchi S, Doi Y (2004) An extra large insertion in the polyhydroxyalkanoate synthase from Delftia acidovorans DS-17: its deletion effects and relation to cellular proteolysis. FEMS Microbiol Lett 231:77-83
32. Valentin H, Steinbüchel A (1994) Application of enzymatically synthesized short-chain-length hydroxy fatty acid coenzyme A thioesters for assay of polyhydroxyalkanoic acid synthases. Appl Microbiol Biotechnol 40:699-709
33. Zhang S, Yasuo T, Lenz RW, Goodwin S (2000) Kinetic and mechanistic characterization of the polyhydroxybutyrate synthase from Ralstonia eutropha. Biomacromolecules 1:244-251