Enatiomerically pure hydroxycarboxylic acids: Current approaches and future perspectives

Applied Microbiology and Biotechnology

Volumn 87, Issue 1, 2010, Pages 41-52

  Ren, Qun ^a   Ruth, Katinka ^b   Thöny Meyer, Linda ^a   Zinn, Manfred ^a  

^a SWISS FEDERAL LABORATORIES FOR MATERIALS SCIENCE AND TECHNOLOGY   (Switzerland)

^b METROHM AG   (Switzerland)

Author keywords

Biotechnological processes; Chiral compounds; Polyhydroxyalkanotes (PHAs); R hydroxycarboxylic acids

Indexed keywords

BIOLOGICAL ACTIVITIES; BIOTECHNOLOGICAL PROCESS; CHIRAL CHEMICALS; CHIRAL COMPOUNDS; EFFICIENT METHOD; ENANTIOMERICALLY PURE COMPOUNDS; FUTURE PERSPECTIVES; INDUSTRIAL SYNTHESIS; LARGE-SCALE PRODUCTION; POLYHYDROXYALKANOTES; POLYHYDROXYALKANOTES (PHAS); PRODUCTION PROCESS; RENEWABLE CARBON SOURCES;

BIOTECHNOLOGY; ELECTRON TRANSITIONS; ENANTIOMERS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ACIDS;

12 HYDROXY 13 HYDROXYMETHYL 3,5,7 TRIMETHYLTETRADECA 2,4 DIENEDIOIC ACID 12,14 LACTONE; 3 HYDROXYBUTYRIC ACID; 3 HYDROXYBUTYRIC ACID METHYL ESTER; 3 HYDROXYHEPT 6 ENOATE; 3 HYDROXYHEPTANOATE; 3 HYDROXYHEXANOATE; 3 HYDROXYNONANOATE; 3 HYDROXYOCTANOATE; 3 HYDROXYUNDEC 10 ENOATE; 3 HYDROXYUNDECANOATE; ANTIBIOTIC AGENT; BETA AMINO ACID; BIOFUEL; CARBOXYLIC ACID; COPOLYMER; DEPSIPEPTIDE; GLOBOMYCIN; HYDROXYCARBOXYLIC ACID; HYDROXYMETHYLGLUTARYL COENZYME A REDUCTASE INHIBITOR; POLYESTER; PSEUDOMYCIN; ROSUVASTATIN; SIMVASTATIN; SPHINGOFUNGIN D; SPHINGOFUNGIN F; STEVASTELIN B; STEVASTELIN B3; SULFOBACIN A; TETRAHYDROLIPSTATIN; UNCLASSIFIED DRUG; UNINDEXED DRUG;

BIOLOGICAL ANALYSIS; BIOTECHNOLOGY; ESTER; FUTURE PROSPECT; INDUSTRIAL PRODUCTION;

BACTERIUM; BIOTECHNOLOGICAL PRODUCTION; BIOTRANSFORMATION; CARBON SOURCE; CHIRALITY; ENANTIOMER; ENZYMATIC DEGRADATION; METABOLIC ENGINEERING; MICROBIAL DEGRADATION; NONHUMAN; SHORT SURVEY; SYNTHESIS; BACTERIA; BIOTECHNOLOGY; CHEMISTRY; EVALUATION STUDY; GENETICS; METABOLISM; PROCEDURES; STEREOISOMERISM; TRENDS;

BACTERIA; BIOTECHNOLOGY; CARBOXYLIC ACIDS; POLYESTERS; STEREOISOMERISM;

EID: 77952890734     PISSN: 01757598     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00253-010-2530-6     Document Type: Short Survey

References (140)

1. JD Aebi DT Deyo QS Chong D Guillaume B Dunlap DH Rich 1990 Synthesis, conformation, and immunosuppressive activities of 3 analogs of cyclosporine-a modified in the 1-position J Med Chem 33 999 1009 1:CAS:528:DyaK3cXhtF2nsbo%3D
2. H Arslan A Mentes B Hazer 2004 Synthesis and characterization of diblock, triblock, and multiblock copolymers containing poly(3-hydroxybutyrate) units J Appl Polym Sci 94 1789 1796 1:CAS:528:DC%2BD2cXotl2hsr4%3D
3. Becker GOH, Berger W, Domschke G (2001) Organikum organisch-chemisches Grundpraktikum. Wiley-VCH, Weinheim
4. Bommarius AS, Riebel BR (2004) Biocatalysis-fundamentals and applications. Wiley-VCH, Weinheim
5. HC Brown PV Ramachandran 1991 The boron approach to asymmetric-synthesis Pure Appl Chem 63 307 316 1:CAS:528:DyaK3MXht1Sqtro%3D
6. BP Calabia Y Tokiwa 2006 A novel PHB depolymerase from a thermophilic Streptomyces sp Biotechnol Lett 28 383 388 1:CAS:528:DC%2BD28XjsV2gs7c%3D
7. GQ Chen 2009 A microbial polyhydroxyalkanoates (PHA) based bio- and materials industry Chem Soc Rev 38 2434 2446 1:CAS:528:DC%2BD1MXovVSns7k%3D
8. GQ Chen Q Wu 2005 The application of polyhydroxyalkanoates as tissue engineering materials Biomaterials 26 6565 6578 1:CAS:528:DC%2BD2MXms1Okurg%3D (Pubitemid 41021750)
9. GQ Chen Q Wu 2005 Microbial production and applications of chiral hydroxyalkanoates Appl Microbiol Biotechnol 67 592 599 1:CAS:528: DC%2BD2MXkvFSrtLg%3D
10. YCP Chiang SS Yang JV Heck JC Chabala MN Chang 1989 Total synthesis of L-659, 699, a novel inhibitor of cholesterol-biosynthesis J Org Chem 54 5708 5712 1:CAS:528:DyaL1MXmtlans74%3D
11. T Chiba T Nakai 1985 A synthetic approach to (+)-thienamycin from methyl (R)-3-hydroxybutanoate. A new entry to (3R, 4R)-3-[(R)-1-hydroxyethyl]-4- acetoxy-2-azetidinone Chem Lett 14 651 654
12. A Chung Q Liu SP Ouyang Q Wu GQ Chen 2009 Microbial production of 3-hydroxydodecanoic acid by pha operon and fadBA knockout mutant of Pseudomonas putida KT2442 harboring tesB gene Appl Microbiol Biotechnol 83 513 519 1:CAS:528:DC%2BD1MXmt1Sju7c%3D
13. WJ Colucci RD Tung JA Petri DH Rich 1990 Synthesis of D-lysine-8-cyclosporine A-further characterization of Bop-Cl in the 2-7 hexapeptide fragment synthesis J Org Chem 55 2895 2903 1:CAS:528: DyaK3cXhvF2is7g%3D
14. PJ Crocker MJ Miller 1995 Oxidative free-radical cyclization as a method for annulating β-lactams: syntheses of functionalized carbacephams J Org Chem 60 6176 6179 1:CAS:528:DyaK2MXotlOgsbc%3D
15. LI de Eugenio P Garcia JM Luengo JM Sanz J San Roman JL Garcia MA Prieto 2007 Biochemical evidence that phaZ gene encodes a specific intracellular medium chain length polyhydroxyalkanoate depolymerase in Pseudomonas putida KT2442-characterization of a paradigmatic enzyme J Biol Chem 282 4951 4962
16. G de Roo MB Kellerhals Q Ren B Witholt B Kessler 2002 Production of chiral R-3-hydroxyalkanoic acids and R-3-hydroxy alkanoic acid methylesters via hydrolytic degradation of polyhydroxyalkanoate synthesized by pseudomonads Biotech Bioeng 77 717 722
17. A Deraadt N Klempier K Faber H Griengl 1992 Chemoselective enzymatic-hydrolysis of aliphatic and alicyclic nitriles J Chem Soc Perkin Trans 1 1 137 140
18. O Dirat C Kouklovsky Y Langlois 1998 Oxazoline N-oxide-mediated [2+3] cycloadditions: application to a total synthesis of the hypocholesterolemic agent 1233A J Org Chem 63 6634 6642 1:CAS:528:DyaK1cXls12msbo%3D
19. C Faveau M Mondon JP Gesson T Mahnke S Gebhardt U Koert 2006 Synthetic studies on a phenyl-laulimalide analogue Tetrahedron Lett 47 8305 8308 1:CAS:528:DC%2BD28XhtFWjtbzF
20. LJR Foster ES Stuart A Tehrani RW Lenz RC Fuller 1996 Intracellular depolymerase and polyhydroxyoctanoate granule integrity in Pseudomonas oleovorans Int J Biol Macromol 19 177 183 1:CAS:528:DyaK28Xms1Shsr0%3D
21. LJR Foster RW Lenz RC Fuller 1999 Intracellular depolymerase activity in isolated inclusion bodies containing polyhydroxyalkanoates with long alkyl and functional substituents in the side chain Int J Biol Macromol 26 187 192 1:CAS:528:DyaK1MXntVWlsrc%3D
22. HJ Gao QN Wu GQ Chen 2002 Enhanced production of D-(-)-3-hydroxybutyric acid by recombinant Escherichia coli FEMS Microbiol Lett 213 59 65 1:CAS:528:DC%2BD38XlsVOrurw%3D
23. M Gavrilescu Y Chisti 2005 Biotechnology-a sustainable alternative for chemical industry Biotechnol Adv 23 471 499 1:CAS:528:DC%2BD2MXhtVWhu7zN
24. Gokarn RR, Selifonova OV, Jessen HJ, Steven JG, Selmer T, Buckel W (2001) 3-Hydroxypropionic acid and other organic compounds. Patent PCT/US2001/043607
25. CT Goodhue JR Schaeffe 1971 Preparation of L(+) beta-hydroxyisobutyric acid by bacterial oxidation of isobutyric acid Biotechnol Bioeng 13 203 214 1:CAS:528:DyaE3MXktleqsbc%3D
26. G Graner M Hamberg J Meijer 2003 Screening of oxylipins for control of oilseed rape (Brassica napus) fungal pathogens Phytochemistry 63 89 95 1:CAS:528:DC%2BD3sXit1Knt7o%3D
27. P Gupta SV Naidu P Kumar 2004 A practical enantioselective synthesis of massoialactone via hydrolytic kinetic resolution Tetrahedron Lett 45 849 851 1:CAS:528:DC%2BD3sXhtVSiu77K
28. M Hamberg 2005 Hidden stereospecificity in the biosynthesis of divinyl ether fatty acids FEBS J 272 736 743 1:CAS:528:DC%2BD2MXht12huro%3D
29. EC Hann AE Sigmund SK Fager FB Cooling JE Gavagan A Ben-Bassat S Chauhan MS Payne SM Hennessey R DiCosimo 2003 Biocatalytic hydrolysis of 3-hydroxyalkanenitriles to 3-hydroxyalkanoic acids Adv Synth Catal 345 775 782 1:CAS:528:DC%2BD3sXkvF2qtrc%3D
30. J Hasegawa S Hamaguchi M Ogura K Watanabe 1981 Production of beta-hydroxycarboxylic acids from aliphatic carboxylic acids by microorganisms J Ferment Technol 59 257 262 1:CAS:528:DyaL3MXmtFyrur8%3D
31. J Hasegawa M Ogura H Kanema H Kawaharada K Watanabe 1983 Production of D-beta-hydroxycarboxylic acids from the corresponding carboxylic acids by a mutant of Candida rugosa J Ferment Technol 61 37 42 1:CAS:528:DyaL3sXhsVWrsbk%3D
32. M Hattori H Takai M Kinoshita 1978 Syntheses and condensation polymerizations of 3-hydroxybutyric acid-derivatives of pyrimidine-bases Macromol Chem Phys 179 905 913 1:CAS:528:DyaE1cXktVKmu7Y%3D
33. K Hayakawa F Nagatsugi K Kanematsu 1988 Total synthesis of (+)-4-oxo-5, 6, 9, 10-tetradehydro-4, 5-secofuranoeremophilane-5, 1-carbolact one via novel lactone construction through allene intramolecular cyclo-addition J Org Chem 53 860 863 1:CAS:528:DyaL1cXpsVaktQ%3D%3D
34. M Hirama T Noda S Ito 1985 Convenient synthesis of (S)-citronellol of high optical purity J Org Chem 50 127 129 1:CAS:528:DyaL2MXnvFWmtA%3D%3D
35. M Hiramoto K Okada S Nagai 1971 The structure of viscosin, a peptide antibiotic-syntheses of D-3-hydroxyacyl-L-leucine hydrazides related to viscosin Chem Pharm Bull 19 1308 1314 1:CAS:528:DyaE3MXltlSisrw%3D
36. M Ikunaka 2003 A process in need is a process indeed: scalable enantioselective synthesis of chiral compounds for the pharmaceutical industry Chem Eur J 9 379 388
37. M Inoue M Nakada 2007 Structure elucidation and enantioselective total synthesis of the potent HMG-CoA reductase inhibitor FR901512 via catalytic asymmetric Nozaki-Hiyama reactions J Am Chem Soc 129 4164 4165 1:CAS:528:DC%2BD2sXivF2jtrg%3D
38. N Irako T Shioiri 1998 Total synthesis of sulfobacin A (Flavocristamide B) Tetrahedron Lett 39 5793 5796 1:CAS:528:DyaK1cXkvFGlur8%3D
39. Y Ito K Ishida S Okada M Murakami 2004 The absolute stereochemistry of anachelins, siderophores from the cyanobacterium Anabaena cylindrica Tetrahedron 60 9075 9080 1:CAS:528:DC%2BD2cXnsVKisL0%3D
40. K Jaeger A Steinbüchel D Jendrossek 1995 Substrate specificities of bacterial polyhydroxyalkanoate depolymerases and lipases-bacterial lipases hydrolyze poly(omega-hydroxyalkanoates) Appl Environ Microbiol 61 3113 3118 1:CAS:528:DyaK2MXnt1ahsrw%3D
41. D Jendrossek R Handrick 2002 Microbial degradation of polyhydroxyalkanoates Annu Rev Microbiol 56 403 432 1:CAS:528: DC%2BD38Xos1GisLw%3D
42. R Kaiser D Lamparsky 1976 Lactone of 5-hydroxy-cis-2-cis-7-decadienic acid and other lactones from essential oils of Polianthes tuberosa L flowers Tetrahedron Lett 17 1659 1660
43. Y Kashiwaya T Takeshima N Mori K Nakashima K Clarke RL Veech 2000 D-β-Hydroxybutyrate protects neurons in models of Alzheimer's and Parkinson's disease Proc Natl Acad Sci U S A 97 5440 5444 1:CAS:528: DC%2BD3cXjsVWmsr8%3D
44. M Katayama A Hiraide H Sugimoto T Yoshioka T Sugimoto 1994 Effect of ketone bodies on hyperglycemia and lactic acidemia in hemorrhagic stress J Parenter Enteral Nutr 18 442 446 1:STN:280:DyaK2M7hsFaksw%3D%3D
45. O Katoh T Sugai H Ohta 1994 Application of microbial enantiofacially selective hydrolysis in natural product synthesis Tetrahedron-Asymmetry 5 1935 1944 1:CAS:528:DyaK2MXhvFWksrs%3D
46. Keri V, Szabo C, Arvai E, Aronhime J (2007) Novel forms of pravastatin sodium. Patent US2005288370
47. T Kiho M Nakayama H Kogen 2003 Total synthesis and NMR conformational study of signal peptidase II inhibitors, globomycin and SF-1902 A(5) Tetrahedron 59 1685 1697 1:CAS:528:DC%2BD3sXht1yqtLw%3D
48. T Kiho M Nakayama K Yasuda S Miyakoshi M Inukai H Kogen 2003 Synthesis and antimicrobial activity of novel globomycin analogues Bioorg Med Chem Lett 13 2315 2318 1:CAS:528:DC%2BD3sXkvVGrur8%3D
49. T Kiho M Nakayama K Yasuda S Miyakoshi M Inukai H Kogen 2004 Structure-activity relationships of globomycin analogues as antibiotics Bioorg Med Chem 12 337 361 1:CAS:528:DC%2BD2cXjsVOktg%3D%3D
50. DY Kim HW Kim MG Chung YH Rhee 2007 Biosynthesis, modification, and biodegradation of bacterial medium-chain-length polyhydroxyalkanoates J Microbiol 45 87 97
51. T Kobayashi Y Hori 1993 Synthesis of biodegradable polyesters by polycondensation of methyl (R)-3-hydroxybutyrate and methyl (R)-3- hydroxyvalerate Macromol Rapid Commun 14 785 790 1:CAS:528:DyaK2cXjtFertg%3D%3D
52. S Kobayashi M Matsumura T Furuta T Hayashi S Iwamoto 1997 The asymmetric synthesis of sphingofungin F and the determination of its stereochemistry Synlett 3 301 303
53. E Kodicek 1949 The effect of unsaturated fatty acids on gram-positive bacteria Symp Soc Exp Biol 3 217 232
54. O Labeeuw P Phansavath JP Genet 2004 Total synthesis of sulfobacin A through dynamic kinetic resolution of a racemic [β]-keto-[α]-amino ester hydrochloride Tetrahedron: Asymmetry 15 1899 1908 1:CAS:528: DC%2BD2cXkvFymsb0%3D
55. SY Lee 2000 Bacterial polyhydroxyalkanoates Biotechnol Bioeng 49 1 14
56. SY Lee Y Lee 2003 Metabolic engineering of Escherichia coli for production of enantiomerically pure (R)-(-)-hydroxycarboxylic acids Appl Environ Microbiol 69 3421 3426 1:CAS:528:DC%2BD3sXks1Gltbg%3D
57. Lee S, Lee K (2004) Method of preparing statins intermediates. Patent WO/2004/096789
58. SY Lee Y Lee F Wang 1999 Chiral compounds from bacterial polyesters: sugars to plastics to fine chemicals Biotech Bioeng 65 363 368 1:CAS:528:DyaK1MXntVOgt7c%3D
59. Y Lee SH Park IT Lim KB Han SY Lee 2000 Preparation of alkyl (R)-(-)-3-hydroxybutyrate by acidic alcoholysis of poly-(R)-(-)-3- hydroxybutyrate Enzyme Microb Technol 27 33 36 1:CAS:528:DC%2BD3cXktFSjurc%3D
60. SH Lee SJ Park SY Lee SH Hong 2008 Biosynthesis of enantiopure (S)-3-hydroxybutyric acid in metabolically engineered Escherichia coli Appl Microbiol Biotechnol 79 633 641 1:CAS:528:DC%2BD1cXmsFKnsrw%3D
61. RU Lemieux J Giguere 1951 Biochemistry of the ustilaginales: the configurations of some beta-hydroxyacids and the bioreduction of beta-ketoacids Can J Chem 29 678 681 1:CAS:528:DyaG38XivFGlsQ%3D%3D
62. UD Lengweiler MG Fritz D Seebach 1996 Monodisperse linear and cyclic oligo[(R)-3-hydroxybutanoates] containing up to 128 monomeric units Helv Chim Acta 79 670 701 1:CAS:528:DyaK28Xjt1akt7Y%3D
63. Lenz RW, Marchessault RH (2005) Bacterial polyesters: Biosynthesis, biodegradable plastics and biotechnology. Biomacromolecules 6:1-8
64. R Li Q Chen PG Wang QS Qi 2007 A novel-designed Escherichia coli for the production of various polyhydroxyalkanoates from inexpensive substrate mixture Appl Microbiol Biotechnol 75 1103 1109 1:CAS:528:DC%2BD2sXmsVKqtr4%3D
65. Q Liu SP Ouyang A Chung Q Wu GQ Chen 2007 Microbial production of R-3-hydroxybutyric acid by recombinant E. coli harboring genes of phbA, phbB, and tesB Appl Microbiol Biotechnol 76 811 818 1:CAS:528:DC%2BD2sXpslartbc%3D
66. MSG Lopes RCS Rocha SP Zanotto JGC Gomez LF da Silva 2009 Screening of bacteria to produce polyhydroxyalkanoates from xylose World J Microbiol Biotechnol 25 1751 1756 1:CAS:528:DC%2BD1MXhtVygsrjN
67. JE Lynch RP Volante RV Wattley I Shinkai 1987 Synthesis of an HMG-CoA reductase inhibitor-a diastereoselective aldol approach Tetrahedron Lett 28 1385 1388 1:CAS:528:DyaL1cXjslCktw%3D%3D
68. E Marotta I Pagani P Righi G Rosini 1994 Synthesis of methyl-substituted bicyclo[3.2.0]hept-3-en-6-ones and 3, 3a, 4, 6a-tetrahydro-2H-cyclopenta[b] furan-2-ones Tetrahedron 50 7645 7656 1:CAS:528:DyaK2MXitFehtA%3D%3D
69. E Marotta B Piombi P Righi G Rosini 1994 N-bromosuccinimide-induced lactonization of bicyclo[3.2.0]hept-3-en-6-ones J Org Chem 59 7526 7528 1:CAS:528:DyaK2MXhvVentLY%3D
70. E Marotta P Righi G Rosini 1994 A new, effective route to methyl substituted 3, 3a, 4, 6a-tetrahydro-2H-cyclopenta[b]furan-2-ones Tetrahedron Lett 35 2949 2950 1:CAS:528:DyaK2cXksFOhtro%3D
71. CH Martin KLJ Prather 2009 High-titer production of monomeric hydroxyvalerates from levulinic acid in Pseudomonas putida J Biotechnol 139 61 67 1:CAS:528:DC%2BD1cXhsV2ltrrI
72. OR Martin W Zhou XF Wu S Front-Deschamps S Moutel K Schindl P Jeandet C Zbaeren JA Bauer 2006 Synthesis and immunobiological activity of an original series of acyclic lipid a mimics based on a pseudodipeptide backbone J Med Chem 49 6000 6014 1:CAS:528:DC%2BD28XptlOlt7g%3D
73. L Massieu ML Hacesa T Montiela K Hernández-Fonseca 2003 Acetoacetate protects hippocampal neurons against glutamate-mediated neuronal damage during glycolysis inhibition Neuroscience 120 365 378 1:CAS:528:DC%2BD3sXlvVCltr8%3D
74. Morgan B, Burk M (2005) Methods for making simvatatin and intermediates. Patent WO/2005/040107
75. K Mori K Otaka 1994 Synthesis of sphingofungin D and its stereoisomer at C14 Tetrahedron Lett 35 9207 9210 1:CAS:528:DyaK2MXislahu7k%3D
76. LEA Munoz MR Riley 2008 Utilization of cellulosic waste from tequila bagasse and production of polyhydroxyalkanoate (PHA) bioplastics by Saccharophagus degradans Biotechnol Bioeng 100 882 888 1:CAS:528: DC%2BD1cXovFWhu7Y%3D
77. M Nakahata M Imaida H Ozaki T Harada A Tai 1982 The preparation of optically pure 3-hydroxyalkanoic acid-the enantioface-differentiating hydrogenation of the C∈=∈O double-bond with modified Raney-nickel Bull Chem Soc Jpn 55 2186 2189 1:CAS:528:DyaL38XmtFGnurs%3D
78. C Nieman 1954 Influence of trance amounts of fatty acids on the growth of microorganisms Bacteriol Rev 18 147 163 1:CAS:528:DyaG2cXltleiug%3D%3D
79. K Nihei K Hashimoto K Miyairi T Okuno 2005 Enantioselective synthesis of four isomers of 3-hydroxy-4-methyltetradecanoic acid, the constituent of antifungal cyclodepsipeptides W493 A and B Biosci Biotechnol Biochem 69 231 234 1:CAS:528:DC%2BD2MXht1Cisro%3D
80. R Noyori T Ohkuma M Kitamura H Takaya N Sayo H Kumobayashi S Akutagawa 1987 Asymmetric hydrogenation of β-keto carboxylic esters-a practical, purely chemical access to β-hydroxy esters in high enantiomeric purity J Am Chem Soc 109 5856 5858 1:CAS:528:DyaL2sXlslGntL8%3D
81. R Noyori M Kitamura T Ohkuma 2004 Toward efficient asymmetric hydrogenation: architectural and functional engineering of chiral molecular catalysts Proc Natl Acad Sci U S A 101 5356 5362 1:CAS:528:DC%2BD2cXjsVagt7s%3D
82. Numata K, Abe H, Doi Y (2008) Enzymatic processes for biodegradation of poly(hydroxyalkanoate)s crystals. Can J Chem-Rev Can Chim 86:471-483
83. Ohashi T, Hasegawa J (1992a) D-(-)-β-hydroxycarboxylic acids as raw materials for captopril and beta lactams. In: collins AN, Sheldrake GN, Crosby J (eds) Chirality in Industry. John Wiley & Sons Ltd, New York, pp 269-278
84. Ohashi T, Hasegawa J (1992b) New preparative methods for optically active β-hydroxycarboxylic acids. In: Collins AN, Sheldrake G, Crosby J (eds) Chirality in Industry. John Wiley & Sons, New York, pp 249-268
85. SH Park SH Lee SY Lee 2001 Preparation of optically active β-amino acids from microbial polyester polyhydroxyalkanoates J Chem Res-S 11 498 499 1:CAS:528:DC%2BD3MXlslCqsbc%3D
86. SJ Park SY Lee Y Lee 2004 Biosynthesis of (R)-3-hydroxyalkanoic acids by metabolically engineered Escherichia coli Appl Biochem Biotechnol 114 373 379
87. I Paterson AN Hulme 1995 Total synthesis of (-)-ebelactone A and (-)-ebelactone B1 J Org Chem 60 3288 3300 1:CAS:528:DyaK2MXlsl2js7w%3D
88. JM Pons P Kocienski 1989 A synthesis of (-)-tetrahydrolipstatin Tetrahedron Lett 30 1833 1836 1:CAS:528:DyaK3cXhtF2gtLo%3D
89. Q Ren A Grubelnik M Hoerler K Ruth R Hartmann H Felber M Zinn 2005 Bacterial poly(hydroxyalkanoates) as a source of chiral hydroxyalkanoic acids Biomacromolecules 6 2290 2298 1:CAS:528:DC%2BD2MXksVekt7s%3D
90. Ren Zulian Q, Pletscher E, Zinn M, Thöny-Meyer L (2008) Method for the production of R-hydroxycarboxylic acids. Patent WO2008113190
91. DH Rich CQ Sun D Guillaume B Dunlap DA Evans AE Weber 1989 Synthesis, biological activity, and conformational analysis of (2s, 3r, 4s)-mebmt1-cyclosporin, a novel 1-position epimer of cyclosporine A J Med Chem 32 1982 1987 1:CAS:528:DyaL1MXkvFOksrk%3D
92. MJ Rodriguez M Belvo R Morris DJ Zeckner WL Current RK Sachs MJ Zweifel 2001 The synthesis of pseudomycin C via a novel acid promoted side-chain deacylation of pseudomycin A Bioorg Med Chem Lett 11 161 164 1:CAS:528:DC%2BD3MXotlKlsg%3D%3D
93. K Roth 2005 Eine unendliche chemische Geschichte Chem Unserer Zeit 39 212 217
94. K Ruth A Grubelnik R Hartmann T Egli M Zinn Q Ren 2007 Efficient production of (R)-3-hydroxycarboxylic acids by biotechnological conversion of polyhydroxyalkanoates and their purification Biomacromolecules 8 279 286 1:CAS:528:DC%2BD28Xht1GjsbrM
95. A Sandoval E Arias-Barrau F Bermejo L Canedo G Naharro E Olivera J Luengo 2005 Production of 3-hydroxy-n-phenylalkanoic acids by a genetically engineered strain of Pseudomonas putida Appl Microbiol Biotechnol 67 97 105 1:CAS:528:DC%2BD2MXksFagtrg%3D (Pubitemid 40543919)
96. F Sarabia S Chammaa 2005 Synthetic studies on stevastelins-total synthesis of stevastelins B and B3 J Org Chem 70 7846 7857 1:CAS:528: DC%2BD2MXpt1CntLs%3D (Pubitemid 41377489)
97. T Satō 1987 Synthesis of optically active forms of the δ-lactone of 3, 5-dihydroxydecanoic acid Can J Chem 65 2732 2733
98. M Sauer D Porro D Mattanovich P Branduardi 2008 Microbial production of organic acids: expanding the markets Trends Biotechnol 26 100 108 1:CAS:528:DC%2BD1cXhsVCktL8%3D
99. U Schmidt W Siegel 1987 Amino acids and peptides. Synthesis of (4R)-4-((E)-2-butenyl)-4, N-dimethyl-L-threonine (mebmt), the characteristic amino acid of cyclosporine Tetrahedron Lett 28 2849 2852 1:CAS:528: DyaL1cXpsVyrtA%3D%3D
100. SL Schreiber SE Kelly JA Porco T Sammakia EM Suh 1988 Structural and synthetic studies of the spore germination autoinhibitor gloeosporone J Am Chem Soc 110 6210 6218 1:CAS:528:DyaL1cXltFSis7g%3D
101. D Seebach AK Beck R Breitschuh K Job 1993 Direct degradation of the biopolymer poly[(R)-3-hydroxybutyric acid] to (R)-3-hydroxybutanoic acid and its methyl ester Org Synth 71 39 47 1:CAS:528:DyaK2cXktV2js70%3D
102. D Seebach MG Fritz 1999 Detection, synthesis, structure, and function of oligo(3-hydroxyalkanoates): contributions by synthetic organic chemists Int J Biol Macromol 25 217 236 1:CAS:528:DyaK1MXksV2qt7s%3D
103. D Seebach M Albert P Arvidsson M Rueping JV Schreiber 2001 From the biopolymer PHB to biological investigations of unnatural β- and γ-peptides Chimia 55 345 353 1:CAS:528:DC%2BD3MXjs1OlsL0%3D
104. B Seuring D Seebach 1978 Syntheses and determination of the absolute-configurations of norpyrenophorin, pyrenophorin, and vermiculine Liebigs Ann Chem 12 2044 2073
105. RA Sheldon 1996 Biocatalytic vs. chemical synthesis of enantiomerically pure compounds Chimia 50 418 419 1:CAS:528:DyaK28XlvFSiuro%3D
106. M Shiraki T Endo T Saito 2006 Fermentative production of (R)-(-)-3-hydroxybutyrate using 3-hydroxybutyrate dehydrogenase null mutant of Ralstonia eutropha and recombinant Escherichia coli J Biosci Bioeng 102 529 534 1:CAS:528:DC%2BD2sXhs1Oqs74%3D
107. CJ Sih BN Zhou AS Gopalan WR Shieh CS Chen G Girdaukas F Vanmiddlesworth 1984 Enantioselective reductions of beta-keto-esters by bakers-yeast Ann Ny Acad Sci 434 186 193 1:CAS:528:DyaL2MXhsVOnsLs%3D
108. J Spengler F Albericio 2008 Asymmetric synthesis of α-unsubstituted β-hydroxy acids Curr Org Synth 5 151 161 1:CAS:528:DC%2BD1cXot1Omsrg%3D
109. A Steinbüchel HE Valentin 1995 Diversity of bacterial polyhydroxyalkanoic acids FEMS Microbiol Lett 128 219 228
110. Sudesh K, Abe H, Doi Y (2000) Synthesis, structure and properties of polyhydroxyalkanoates: biological polyesters. Prog Polym Sci 25:1503-1555
111. Z Sun J Ramsay M Guay B Ramsay 2009 Fed-batch production of unsaturated medium-chain-length polyhydroxyalkanoates with controlled composition by Pseudomonas putida KT2440 Appl Microbiol Biotech 82 657 662 1:CAS:528: DC%2BD1MXisVWkur8%3D
112. MA Sutter D Seebach 1983 Synthesis of (2E, 4E, 6S, 7R, 10E, 12E, 14S, 15R)-6, 7, 14, 15-tetramethyl-8, 16-dioxa-2, 4, 10, 12-cy-clohexadecatetraene-1, 9-dione-a model system for Elaiophylin Liebigs Ann Chem 6 939 949
113. S Tahara J Mitzutani 1978 Preparation of L-3-hydroxyalkanoic acids by fungal hydration of the corresponding trans-2-alkenoic acids Agric Biol Chem 4 879 883
114. O Tasaki A Hiraide T Shiozaki H Yamamura N Ninomiya H Sugimoto 1999 The dimer and trimer of 3-hydroxybutyrate oligomer as a precursor of ketone bodies for nutritional care J Parenter Enteral Nutr 23 321 325 1:CAS:528: DC%2BD3cXlvFGmtb4%3D
115. PY Tian LA Shang H Ren Y Mi DD Fan M Jiang 2009 Biosynthesis of polyhydroxyalkanoates: current research and development Afr J Biotechnol 8 709 714 1:CAS:528:DC%2BD1MXjsVWgs7o%3D
116. K Tieu C Perier C Caspersen P Teismann DC Wu SD Yan A Naini M Vila V Jackson-Lewis R Ramasamy S Przedborski 2003 D-β-Hydroxybutyrate rescues mitochondrial respiration and mitigates features of Parkinson disease J Clin Invest 112 892 901 1:CAS:528:DC%2BD3sXnsVGntL8%3D
117. R Touati V Ratovelomanana-Vidal B Ben Hassine JP Genet 2006 Synthesis of enantiopure (R)-(-)-massoialactone through ruthenium-SYNPHOS (R) asymmetric hydrogenation Tetrahedron-Asymmetry 17 3400 3405 1:CAS:528:DC%2BD2sXht12qtbk%3D
118. HC Tseng CH Martin DR Nielsen KLJ Prather 2009 Metabolic engineering of Escherichia coli for enhanced production of (R)-and (S)-3-hydroxybutyrate Appl Environ Microbiol 75 3137 3145 1:CAS:528:DC%2BD1MXmsFWisLg%3D
119. M Utaka H Watabu W Higadhi T Sakai S Tsuboi S Torii 1990 Asymmetric reduction of aliphatic short- to long chain beta-keto acids by use of fermenting bakers' yeast J Org Chem 55 3917 3921 1:CAS:528:DyaK3cXksVShsLc%3D
120. F Vanmiddlesworth C Dufresne FE Wincott RT Mosley KE Wilson 1992 Determination of the relative and absolute stereochemistry of sphingofungin A, sphingofungin B, sphingofungin C, and sphingofungin D Tetrahedron Lett 33 297 300 1:CAS:528:DyaK38XhvFCrsrY%3D
121. D Vollbrecht HG Schlegel 1978 Excretion of metabolites by hydrogen bacteria.2. Influences of aeration, ph, temperature, and age of cells Eur J Appl Microbiol Biotechnol 6 157 166 1:CAS:528:DyaE1MXhtVWqsbg%3D
122. D Vollbrecht HG Schlegel 1979 Excretion of metabolites of hydrogen bacteria.3. D(-)-3-hydroxybutanoate Eur J Appl Microbiol Biotechnol 7 259 266 1:CAS:528:DyaE1MXlvV2ns7c%3D
123. D Vollbrecht MA Elnawawy HG Schlegel 1978 Excretion of metabolites by hydrogen bacteria.1. Autotrophic and heterotrophic fermentations Eur J Appl Microbiol Biotechnol 6 145 155 1:CAS:528:DyaE1MXpvFOktw%3D%3D
124. Z Wang C Zhao ME Pierce JM Fortunak 1999 Enantioselective synthesis of β-hydroxycarboxylic acids: direct conversion of β-oxocarboxylic acids to enantiomerically enriched β-hydroxycarboxylic acids via neighboring group control Tetrahedron: Asymmetry 10 225 228 1:CAS:528:DyaK1MXhvFamtb4%3D
125. L Wang W Armbruster D Jendrossek 2007 Production of medium-chain-length hydroxyalkanoic acids from Pseudomonas putida in pH stat Appl Microbiol Biotechnol 75 1047 1053 1:CAS:528:DC%2BD2sXmsVKqtLg%3D
126. A Wohlrab R Lamer MS van Nieuwenhze 2007 Total synthesis of plusbacin A(3): a depsipeptide antibiotic active against vancomycin-resistant bacteria J Am Chem Soc 129 4175 4177 1:CAS:528:DC%2BD2sXjtVClsrk%3D
127. YK Wu YP Sun 2005 Novel chemoselective tosylation of the alcoholic hydroxyl group of syn-α, β-disubstituted β-hydroxy carboxylic acids Chem Commun 14 1906 1908
128. Q Wu Z Zheng JZ Xi HJ Gao GQ Chen 2003 Production of hydroxyalkanoate monomers by microbial fermentation J Chem Eng Jpn 36 1170 1173 1:CAS:528:DC%2BD3sXoslelsb0%3D
129. Xie CH. Yokota A (2005) Reclassification of Alcaligenes latus strains IAM 12599(T) and IAM 12664 and Pseudomonas saccharophila as Azohydromonas lata gen. nov., comb. nov., Azohydromonas australica sp nov and Pelomonas saccharophila gen. nov., comb. nov., respectively. Int J Syst Evol Microbiol 55:2419-2425
130. J Yu L Chen 2008 The greenhouse gas emissions and fossil energy requirement of bioplastics from cradle to gate of a biomass refinery Environ Sci Technol 42 6961 6966 1:CAS:528:DC%2BD1cXpvFSmu7w%3D
131. J Yu H Stahl 2008 Microbial utilization and biopolyester synthesis of bagasse hydrolysates Bioresour Technol 99 8042 8048 1:CAS:528: DC%2BD1cXptVKjtLs%3D
132. MQ Yuan ZY Shi XX Wei QO Wu SF Chen GQ Chen 2008 Microbial production of medium-chain-length 3-hydroxyalkanoic acids by recombinant Pseudomonas putida KT2442 harboring genes fadL, fadD and phaZ FEMS Microbiol Lett 283 167 175 1:CAS:528:DC%2BD1cXnsVCmtro%3D
133. H Zhang ZX Liao JM Yue 2004 Five new sesquiterpenoids from Parasenecio petasitoides HeIv Chim Acta 87 976 982 1:CAS:528:DC%2BD2cXktVSns7Y%3D
134. L Zhang ZY Shi Q Wu GQ Chen 2009 Microbial production of 4-hydroxybutyrate, poly-4-hydroxybutyrate, and poly(3-hydroxybutyrate-co-4- hydroxybutyrate) by recombinant microorganisms Appl Microbiol Biotechnol 84 909 916 1:CAS:528:DC%2BD1MXhtFaqsLvP
135. XJ Zhang RC Luo Z Wang Y Deng GQ Chen 2009 Application of (R)-3-hydroxyalkanoate methyl esters derived from microbial polyhydroxyalkanoates as novel biofuels Biomacromolecules 10 707 711 1:CAS:528:DC%2BD1MXisVKktbk%3D
136. K Zhao G Tian Z Zheng JC Chen GQ Chen 2003 Production of D-(-)-3-hydroxyalkanoic acid by recombinant Escherichia coli FEMS Microbiol Lett 218 59 64 1:CAS:528:DC%2BD3sXhtVCqu7g%3D
137. Y Zhao B Zou ZY Shi Q Wu GQ Chen 2007 The effect of 3-hydroxybutyrate on the in vitro differentiation of murine osteoblast MCM-E1 and in vivo bone formation in ovariectomized rats Biomaterials 28 3063 3073 1:CAS:528: DC%2BD2sXksVersro%3D
138. Z Zheng Q Gong GQ Chen 2004 Novel method for production of 3-hydroxydecanoic acid by recombinant Escherichia coli and Pseudomonas putida Chin J Chem Eng 12 550 555
139. Zlicar M (2007) Process for the synthesis of rosuvastation calcium. Patent WO/2007/017117A1
140. XH Zou HM Li S Wang M Leski YC Yao XD Yang QJ Huang GQ Chen 2009 The effect of 3-hydroxybutyrate methyl ester on learning and memory in mice Biomaterials 30 1532 1541 1:CAS:528:DC%2BD1MXpsFOquw%3D%3D