Enatiomerically pure hydroxycarboxylic acids: current  approaches and future perspectives.
The growing awareness of the importance of chirality in conjunction with biological activity has led to an increasing demand for efficient methods for the industrial synthesis of enantiomerically pure compounds. Polyhydroxyalkanotes (PHAs) are a family of polyesters consisting of over 140 chiral R-hydroxycarboxylic acids (R-HAs), representing a promising source for obtaining chiral chemicals from renewable carbon sources. Although some R-HAs have been produced for some time and certain knowledge of the production processes has been gained, large-scale production has not yet been possible. In this article, through analysis of the current advances in production of these acids, we present guidelines for future developments in biotechnological processes for R-HA production.
Ren
Qun
Q
Swiss Federal Laboratories for Materials Testing and Research (Empa), Laboratory for Biomaterials, 9014 St. Gallen, Switzerland. qun.ren@empa.ch
Ruth
Katinka
K
Thöny-Meyer
Linda
L
Zinn
Manfred
M
D001419:Bacteria / Q000235:genetics / Q000378:metabolism; D001709:Biotechnology / Q000379:methods* / Q000639:trends; D002264:Carboxylic Acids / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D011091:Polyesters / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D013237:Stereoisomerism
D002264:Carboxylic Acids; D011091:Polyesters
Chem Commun (Camb). 2005 Apr 14;(14):1906-8
15795783
FEBS J. 2005 Feb;272(3):736-43
15670154
Annu Rev Microbiol. 2002;56:403-32
12213937
Biomacromolecules. 2005 Jan-Feb;6(1):1-8
15638495
Chem Pharm Bull (Tokyo). 1971 Jul;19(7):1308-14
4998540
Appl Microbiol Biotechnol. 2007 Jul;75(5):1047-53
17401563
Chemistry. 2003 Jan 20;9(2):378-88
12532286
Appl Microbiol Biotechnol. 2008 Jun;79(4):633-41
18461320
Chem Soc Rev. 2009 Aug;38(8):2434-46
19623359
Bioresour Technol. 2008 Nov;99(17):8042-8
18474421
Biotechnol Bioeng. 2002 Mar 20;77(6):717-22
11807767
Int J Biol Macromol. 1999 Jun-Jul;25(1-3):217-36
10416670
Bioorg Med Chem. 2004 Jan 15;12(2):337-61
14723954
Biotechnol Bioeng. 1996 Jan 5;49(1):1-14
18623547
J Biol Chem. 2007 Feb 16;282(7):4951-4962
17170116
Appl Biochem Biotechnol. 2004 Spring;113-116:373-9
15054264
Trends Biotechnol. 2008 Feb;26(2):100-8
18191255
Neuroscience. 2003;120(2):365-78
12890508
J Med Chem. 1990 Mar;33(3):999-1009
2308150
Bacteriol Rev. 1954 Jun;18(2):147-63
13159785
Phytochemistry. 2003 May;63(1):89-95
12657302
Int J Biol Macromol. 1996 Oct;19(3):177-83
8910058
JPEN J Parenter Enteral Nutr. 1994 Sep-Oct;18(5):442-6
7815677
Appl Microbiol Biotechnol. 2007 Jul;75(5):1103-9
17334755
J Am Chem Soc. 1988 Aug 1;110(18):6210-8
22148801
Biomaterials. 2005 Nov;26(33):6565-78
15946738
Biotechnol Bioeng. 1971 Mar;13(2):203-14
5580680
Appl Microbiol Biotechnol. 2005 Apr;67(1):97-105
15800732
Proc Natl Acad Sci U S A. 2004 Apr 13;101(15):5356-62
15034179
J Microbiol. 2007 Apr;45(2):87-97
17483792
J Biosci Bioeng. 2006 Dec;102(6):529-34
17270718
J Biotechnol. 2009 Jan 1;139(1):61-7
18938201
Biomacromolecules. 2007 Jan;8(1):279-86
17206818
Appl Microbiol Biotechnol. 2007 Sep;76(4):811-8
17609944
Biotechnol Lett. 2006 Mar;28(6):383-8
16614903
Appl Microbiol Biotechnol. 2009 Mar;82(4):657-62
19050862
Appl Microbiol Biotechnol. 2009 Oct;84(5):909-16
19434404
J Am Chem Soc. 2007 Apr 11;129(14):4175-7
17371023
Appl Environ Microbiol. 2009 May;75(10):3137-45
19304817
Proc Natl Acad Sci U S A. 2000 May 9;97(10):5440-4
10805800
Appl Environ Microbiol. 1995 Aug;61(8):3113-8
7487042
Environ Sci Technol. 2008 Sep 15;42(18):6961-6
18853816
FEMS Microbiol Lett. 2003 Jan 21;218(1):59-64
12583898
Biomaterials. 2007 Jul;28(20):3063-73
17418401
Enzyme Microb Technol. 2000 Jul 1;27(1-2):33-36
10862899
Appl Environ Microbiol. 2003 Jun;69(6):3421-6
12788745
FEMS Microbiol Lett. 2002 Jul 16;213(1):59-65
12127489
Biotechnol Bioeng. 2008 Aug 1;100(5):882-8
18383127
J Am Chem Soc. 2007 Apr 11;129(14):4164-5
17367147
Biosci Biotechnol Biochem. 2005 Jan;69(1):231-4
15665494
J Med Chem. 2006 Oct 5;49(20):6000-14
17004714
FEMS Microbiol Lett. 2008 Jun;283(2):167-75
18422622
J Med Chem. 1989 Aug;32(8):1982-7
2754718
Biomacromolecules. 2005 Jul-Aug;6(4):2290-8
16004474
Bioorg Med Chem Lett. 2001 Jan 22;11(2):161-4
11206449
Int J Syst Evol Microbiol. 2005 Nov;55(Pt 6):2419-2425
16280506
J Clin Invest. 2003 Sep;112(6):892-901
12975474
Appl Microbiol Biotechnol. 2009 Jun;83(3):513-9
19271216
J Org Chem. 2005 Sep 30;70(20):7846-57
16277304
JPEN J Parenter Enteral Nutr. 1999 Nov-Dec;23(6):321-5
10574479
Int J Biol Macromol. 1999 Nov;26(2-3):187-92
10517528
Appl Microbiol Biotechnol. 2005 Jun;67(5):592-9
15700123
Biotechnol Adv. 2005 Nov;23(7-8):471-99
15919172
Biomaterials. 2009 Mar;30(8):1532-41
19111894
Biotechnol Bioeng. 1999 Nov 5;65(3):363-8
10486136
Bioorg Med Chem Lett. 2003 Jul 21;13(14):2315-8
12824025
Biomacromolecules. 2009 Apr 13;10(4):707-11
19249855