Lipase-catalyzed oligomerization and hydrolysis of alkyl lactates: Direct evidence in the catalysis mechanism that enantioselection is governed by a deacylation step

Biomacromolecules

Volumn 11, Issue 8, 2010, Pages 2008-2015

  Ohara, Hitomi ^a   Onogi, Akihisa ^a   Yamamoto, Masafumi ^a   Kobayashi, Shiro ^a  

^a KYOTO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL GROUP; ALKYL GROUPS; BUTYL GROUP; D-ISOMERS; D-LACTATE; DEACYLATION; ENANTIOSELECTION; HEPTAMERS; HIGH YIELD; L-LACTATE; LIPASE CATALYSIS; NUCLEOPHILIC ATTACK; RATE DETERMINING STEP;

ACYLATION; ALKYLATION; CATALYSIS; HYDROCARBONS; HYDROLYSIS; ISOMERS; LACTIC ACID; MONOMERS; OLIGOMERS; ORGANIC ACIDS; ORGANIC POLYMERS; REACTION RATES;

OLIGOMERIZATION;

LACTIC ACID DERIVATIVE; TRIACYLGLYCEROL LIPASE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DEACYLATION; ENANTIOSELECTIVITY; HYDROLYSIS; OLIGOMERIZATION; PRIORITY JOURNAL;

ACYLATION; BIOCATALYSIS; HYDROLYSIS; LACTATES; LIPASE; MAGNETIC RESONANCE SPECTROSCOPY; POLYMERS; STEREOISOMERISM;

EID: 77955581599     PISSN: 15257797     EISSN: 15264602     Source Type: Journal    
DOI: 10.1021/bm1003674     Document Type: Article

References (52)

1. Ishimoto, K.; Arimoto, M.; Ohara, H.; Kobayashi, S.; Ishii, M.; Morita, K.; Yamashita, H.; Yabuuchi, N. Biomacromolecules 2009, 10, 2719-2723
2. Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and Practice; Oxford University Press: New York, 1998.
3. Kobayashi, S. J. Polym. Sci., Part A: Polym. Chem. 1999, 37, 3041-3056
4. Kobayashi, S.; Uyama, H.; Kimura, S. Chem. Rev. 2001, 101, 3793-3818
5. Kobayashi, S.; Uyama, H.; Takamoto, T. Biomacromolecules 2000, 1, 3-5
6. Tsujimoto, T.; Ikeda, R.; Uyama, H.; Kobayashi, S. Macromol. Chem. Phys. 2001, 202, 3420-3425
7. Mahapatro, A.; Kumar, A.; Gross, R. A. Biomacromolecules 2004, 5, 62-68
8. Puskas, J. E.; Sen, M. Y.; Kasper, J. R. J. Polym. Sci., Part A: Polym. Chem. 2008, 46, 3024-3028
9. Kobayashi, S. Macromol. Rapid Commun. 2009, 30, 137-166
10. Puskas, J. E.; Sen, M. Y.; Seo, K.-S. J. Polym. Sci., Part A: Polym. Chem. 2009, 47, 2959-2976
11. Kobayashi, S.; Makino, A. Chem. Rev. 2009, 109, 5288-5353
12. Kobayashi, S. Proc. Jpn. Acad. B 2010, 86, 338-365
13. Dechy-Cabaret, O.; Martin-Vaca, B.; Bourissou, D. Chem. Rev. 2004, 104, 6147-6176
14. Moon, S. I.; Lee, C. W.; Miyamoto, M.; Kimura, Y. J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 1673-1679
15. Moon, S. I.; Lee, C. W.; Taniguchi, I.; Miyamoto, M.; Kimura, Y. Polymer 2001, 42, 5059-5062
16. Tsuji, H.; Ikada, Y. Polym. Deg. Stab. 2000, 67, 179-189
17. Fukushima, K.; Kimura, Y. Macromol. Symp. 2005, 224, 133-144
18. Fukushima, K.; Furuhashi, Y.; Sogo, K.; Miura, S.; Kimura, Y. Macromol. Biosci. 2005, 5, 21-29
19. Fukushima, K.; Chang, Y.-H.; Kimura, Y. Macromol. Biosci. 2007, 7, 829-835
20. Gupta, B.; Revagade, N.; Hilborn, J. Prog. Polym. Sci. 2007, 32, 455-482
21. Fukushima, K.; Kimura, Y. J. Polym. Sci., Part A: Polym. Chem. 2008, 46, 3714-3722
22. Hirata, M.; Kimura, Y. Polymer 2008, 49, 2656-2661
23. Kakuta, M.; Hirata, M.; Kimura, Y. J. Macromol. Sci., Part C: Polym. Rev. 2009, 49, 1-34
24. Hans, M.; Keul, H.; Moeller, M. Macromol. Biosci. 2009, 9, 239-247
25. Gross, R. A.; Kumar, A.; Kalra, B. Chem. Rev. 2001, 101, 2097-2124
26. Matsumura, S. Macromol. Biosci. 2002, 2, 105-126
27. Albertsson, A. C.; Varma, I. K. Biomacromolecules 2003, 4, 1466-1486
28. Varma, I. K.; Albertsson, A. C.; Rajkhowa, R.; Srivastava, R. K. Prog. Polym. Sci. 2005, 30, 949-981
29. Matsumura, S.; Mabuchi, K.; Toshima, K. Macromol. Rapid Commun. 1997, 18, 477-482
30. Uyama, H.; Takeya, K.; Kobayashi, S. Proc. Jpn. Acad. B 1993, 69, 203-207
31. Matsumura, S.; Tsukada, T.; Toshima, K. Int. J. Biol. Macromol. 1999, 25, 161-167
32. Wahlberg, J.; Persson, P. V.; Olsson, T.; Hedenstrom, E.; Iversen, T. Biomacromolecules 2003, 4, 1068-1071
33. Huijser, S.; Staal, B. B. P.; Huang, J.; Duchateau, R.; Koning, C. E. Biomacromolecules 2006, 7, 2465-2469
34. Bonduelle, C.; Martin-Vaca, B.; Bourissou, D. Biomacromolecules 2009, 10, 3069-3073
35. Lehninger, A. L. Biochemistry; Worth Publishers, Inc.: New York, 1970; p 157.
36. From, M.; Adlercreutz, P.; Mattiasson, B. Biotechnol. Lett. 1997, 19, 315-319
37. Uppenberg, J.; Hansen, M. T.; Patkar, S.; Jones, T. A. Structure 1994, 2, 293-308
38. Anderson, E. M.; Karin, M.; Kirk, O. Biocatal. Biotransform. 1998, 16, 181-204
39. Gotor-Fernandez, V.; Busto, E.; Gotor, V. Adv. Synth. Catal. 2006, 348, 797-812
40. Kikuchi, H.; Uyama, H.; Kobayashi, S. Macromolecules 2000, 33, 8971-8975
41. Peeters, J.; Palmans, A. R. A.; Veld, M.; Scheijen, F.; Heise, A.; Meijer, E. W. Biomacromolecules 2004, 5, 1862-1868
42. Peeters, J. W.; van Leeuwen, O.; Palmans, A. R. A.; Meijer, E. W. Macromolecules 2005, 38, 5587-5592
43. Hilker, I.; Rabani, G.; Verzijl, G. K. M.; Palmans, A. R. A.; Heise, A. Angew. Chem., Int. Ed. 2006, 45, 2130-2132
44. van As, B. A. C.; van Buijtenen, J.; Heise, A.; Broxterman, Q. B.; Verzijl, G. K. M.; Palmans, A. R. A.; Meijer, E. W. J. Am. Chem. Soc. 2005, 127, 9964-9965
45. Kobayashi, S. Macromol. Symp. 2006, 240, 178-185
46. van Buijtenen, J.; van As, B. A. C.; Meuldijk, J.; Palmans, A. R. A.; Vekemans, J.; Hulshof, L. A.; Meijer, E. W. Chem. Commun. 2006, 3169-3171
47. van Buijtenen, J.; van As, B. A. C.; Verbruggen, M.; Roumen, L.; Vekemans, J.; Pieterse, K.; Hilbers, P. A. J.; Hulshof, L. A.; Palmans, A. R. A.; Meijer, E. W. J. Am. Chem. Soc. 2007, 129, 7393-7398
48. Jones, J. B. Tetrahedron 1986, 42, 3351-3403
49. Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994.
50. Faber, K. Biotransformations in Organic Chemistry, 5th ed.; Springer Verlag: New York, 2004.
51. Carcia-Urdiales, E.; Alfonso, I.; Gotor, V. Chem. Rev. 2005, 105, 313-354
52. van Dongen, S. F. M.; de Hoog, H.-P. M.; Peters, R. J. R. W.; Nallani, M.; Nolte, R. J. M.; Hest, J. C. M. Chem. Rev. 2009, 109, 6212-6274