Investigation of the enzymatic cleavage of diastereomeric oligo(3-hydroxybutanoates) containing two to eight HB units. A model for the stereoselectivity of PHB depolymerase from Alcaligenes faecalis T1

Macromolecules

Volumn 32, Issue 6, 1999, Pages 1777-1784

  Bachmann, Beat M ^a   Seebach, Dieter ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

BIODEGRADATION; ENZYMES; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MICROORGANISMS; MOLECULAR ORIENTATION; MONOMERS; OLIGOMERS;

ALCALIGENES FAECALIS; POLYHYDROXYBUTANOATE; STEREOSELECTIVITY;

ORGANIC POLYMERS;

EID: 0032633718     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma981496w     Document Type: Article

References (20)

1. Bachman, B. M. Ph.D. Thesis, ETH Zürich, 1997, # 12074.
2. Doi, Y. Microbial Polyesters; VCH: Weinheim, 1990. Steinbüchel, A. Nachr. Chem. Techn. Lab. 1991, 39, 1112. Müller, H.-M.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1993, 32 (4), 477-502. Seebach, D.; Brunner, A.; Bachmann, B. M.; Hoffmann, T.; Kühnle, F. N. M.; Lengweiler, U. D. Biopolymers and -oligomers of (R)-3-Hydroxyalkanoic Acids - Contributions of Organic Chemists; Ernst Schering Research Foundation: Berlin, 1995. See also: the Congress volumes of the symposia on PHB in Sitges 1990, Montpellier 1991, Göttingen 1992, Montreal 1994, and Davos 1996.
3. Doi, Y. Microbial Polyesters; VCH: Weinheim, 1990. Steinbüchel, A. Nachr. Chem. Techn. Lab. 1991, 39, 1112. Müller, H.-M.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1993, 32 (4), 477-502. Seebach, D.; Brunner, A.; Bachmann, B. M.; Hoffmann, T.; Kühnle, F. N. M.; Lengweiler, U. D. Biopolymers and -oligomers of (R)-3-Hydroxyalkanoic Acids - Contributions of Organic Chemists; Ernst Schering Research Foundation: Berlin, 1995. See also: the Congress volumes of the symposia on PHB in Sitges 1990, Montpellier 1991, Göttingen 1992, Montreal 1994, and Davos 1996.
4. Doi, Y. Microbial Polyesters; VCH: Weinheim, 1990. Steinbüchel, A. Nachr. Chem. Techn. Lab. 1991, 39, 1112. Müller, H.-M.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1993, 32 (4), 477-502. Seebach, D.; Brunner, A.; Bachmann, B. M.; Hoffmann, T.; Kühnle, F. N. M.; Lengweiler, U. D. Biopolymers and -oligomers of (R)-3-Hydroxyalkanoic Acids - Contributions of Organic Chemists; Ernst Schering Research Foundation: Berlin, 1995. See also: the Congress volumes of the symposia on PHB in Sitges 1990, Montpellier 1991, Göttingen 1992, Montreal 1994, and Davos 1996.
5. Doi, Y. Microbial Polyesters; VCH: Weinheim, 1990. Steinbüchel, A. Nachr. Chem. Techn. Lab. 1991, 39, 1112. Müller, H.-M.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1993, 32 (4), 477-502. Seebach, D.; Brunner, A.; Bachmann, B. M.; Hoffmann, T.; Kühnle, F. N. M.; Lengweiler, U. D. Biopolymers and -oligomers of (R)-3-Hydroxyalkanoic Acids - Contributions of Organic Chemists; Ernst Schering Research Foundation: Berlin, 1995. See also: the Congress volumes of the symposia on PHB in Sitges 1990, Montpellier 1991, Göttingen 1992, Montreal 1994, and Davos 1996.
6. Doi, Y. Microbial Polyesters; VCH: Weinheim, 1990. Steinbüchel, A. Nachr. Chem. Techn. Lab. 1991, 39, 1112. Müller, H.-M.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1993, 32 (4), 477-502. Seebach, D.; Brunner, A.; Bachmann, B. M.; Hoffmann, T.; Kühnle, F. N. M.; Lengweiler, U. D. Biopolymers and -oligomers of (R)-3-Hydroxyalkanoic Acids - Contributions of Organic Chemists; Ernst Schering Research Foundation: Berlin, 1995. See also: the Congress volumes of the symposia on PHB in Sitges 1990, Montpellier 1991, Göttingen 1992, Montreal 1994, and Davos 1996.
7. Jendrossek, D.; Schirmer, A.; Schlegel, H. G. Appl. Microbiol. Biotechnol. 1996, 46, 451-463. Brandl, H.; Bachofen, R.; Mayer, J.; Wintermantel, E. Can. J. Microbiol. 1995, 41 (suppl.), 143-153.
8. Jendrossek, D.; Schirmer, A.; Schlegel, H. G. Appl. Microbiol. Biotechnol. 1996, 46, 451-463. Brandl, H.; Bachofen, R.; Mayer, J.; Wintermantel, E. Can. J. Microbiol. 1995, 41 (suppl.), 143-153.
9. Tanio, T.; Fukui, T.; Shirakura, Y.; Saito, T.; Tomita, K.; Kaiho, T.; Masamune, S. Eur. J. Biochem. 1982, 124, 71-77.
10. Saito, T.; Suzuki, K.; Yamamoto, J.; Fukui, T.; Miwa, K.; Tomita, K.; Nakanishi, S.; Odani, S.; Suzuki, J.-I.; Ishikawa, K. J. Bacteriol. 1989, 171, 184-189.
11. Shirakura, Y.; Fukui, T.; Saito, T.; Okamoto, Y.; Narikawa, T.; Koide, K.; Tomita, K.; Takemasa, T.; Masamune, S. Biochim. Biophys. Acto 1986, 880, 46-53.
12. For our previous investigation of all-(R)-OHB degradation by a whole-cell preparation from Acidovorax delafieldii, see: Brandl, H.; Aeberli, B.; Bachofen, R.; Schwegler, I.; Müller, H.-M.; Bürger, M. H.; Hoffmann, T.; Lengweiler, U. D.; Seebach, D. Can. J. Microbiol. 1995, 41 (suppl.), 180-186.
13. Bachmann, B. M.; Seebach, D. Helv. Chim. Acta 1998, 81, 2430-2461.
14. Hocking, P. J.; Marchessault, R. H.; Timmins, M. R.; Lenz, R. W.; Fuller, R. C. Macromolecules 1996, 29, 2472-2478.
15. Walter, T.; Augusta, J.; Müller, R.-J.; Widdecke, H.; Klein, J. Enzyme Microb. Technol. 1995, 17, 218-224.
16. 7 to attack OHBs in an endo fashion was shown earlier by the degradation of cyclic all-(R)-OHBs.
17. For a review article about the influence of substrate crystalunity on the rate of PHB degradation, see: Kemnitzer, J. E.; McCarthy, S. P.; Gross, R. A. Macromolecules 1992, 25, 1221.
18. Shirakura, Y.; Fukui, T.; Tanio, T.; Nakayama, K.; Matsuno, R.; Tomita, K. Biochim. Biophys. Acta 1983, 748, 331-339.
19. Abe, H.; Matsubara, I.; Doi, Y.; Hori, Y.; Yamaguchi, A. Macromolecules 1994, 24, 6018-6025.
20. Hocking, P. J.; Marchessault, R. H. Macromol. Rapid Commun. 1994, 15, 447-452.