Biodegradation of Nylon and other Synthetic Polyamides
Part 9. Miscellaneous Biopolymers and Biodegradation of Polymers
Prof. Dr. Seiji Negoro,
Prof. Dr. Seiji Negoro
- [email protected]
- +81-792-67-4891 | Fax: +81-792-67-4891
Himeji Institute of Technology, Department of Applied Chemistry, Faculty of Engineering, 2167 Shosha, Himeji, Hyogo, Japan, 671-2201
Search for more papers by this authorProf. Dr. Seiji Negoro,
Prof. Dr. Seiji Negoro
- [email protected]
- +81-792-67-4891 | Fax: +81-792-67-4891
Himeji Institute of Technology, Department of Applied Chemistry, Faculty of Engineering, 2167 Shosha, Himeji, Hyogo, Japan, 671-2201
Search for more papers by this authorAbstract
- Introduction
- Historical Outline
- Chemical Structures, and Preparation of Nylon Oligomers
- Cyclic Oligomers of 6-Aminohexanoate
- Linear Oligomers of 6-Aminohexanoate and their Related Compounds
- Production and Main Applications of Nylon
- Biodegradation
- Biodegradation of Polyamides
- Biodegradation of ɛ-Caprolactam
- Biodegradation of Nylon Oligomer
- Biochemistry of Nylon Oligomer Biodegradation
- Plasmid Dependence of Nylon Oligomer-Degrading Enzymes
- Nucleotide Sequence of pOAD2
- Amino Acid Alterations and Catalytic Activity of Nylon Oligomer-Degrading Enzymes
- Substrate Specificity of EII, EII′ and their Hybrid Enzymes
- Experimental Evolution of Nylon Oligomer-Degrading Enzymes
- Molecular Basis for Adaptation toward a Xenobiotic Compound
- Outlook and Perspectives
- Patents
References
- Alloing, G., Trombe, M. C., Claverys, J. P. (1990) The ami locus of the gram-positive bacterium Streptococcus pneumoniae is similar to binding protein-dependent transport operons of gram-negative bacteria, Molec. Microbiol. 4, 633–644.
- Alvarez, E., Meesschaert, B., Montenegro, E., Gutierrez, S., Diez, B., Barredo, J. L., Martin, J. F. (1993) The isopenicillin-N acyltransferase and isopenicillin-N amidohydrolase, 6-amino-penicillanic acid acyltransferase and penicillin amidase activities, all of which are encoded by the single penDE gene, Eur. J. Biochem. 215, 323–332.
- Boronin, A. M., Naumova, R. P., Grishenkov, V. G., Ilijinskaya, O. N. (1984) Plasmids specifying ɛ-caprolactam degradation in Pseudomonas strains, FEMS Microbiol. Lett. 22, 167–170.
- Clarke, P. H., Slater, J. H. (1986) Evolution of enzyme structure and function in Pseudomonas, in: The Bacteria, Vol. 10. The Biology of Pseudomonas ( J. R. Sokatch, Ed.), Orlando, Florida: Academic Press, Inc., 71–144.
- Davis, M. A., Martin, K. A., Austin, S. J. (1992) Biochemical activities of the parA partition protein of the P1 plasmid, Mol. Microbiol. 6, 1141–1147.
- Deguchi, T., Kitaoka, Y., Kakezawa, M., Nishida, T. (1998) Purification and characterization of a nylon-degrading enzyme, Appl. Environ. Microbiol. 64, 1366–1371.
- Foster, P. L., Trimarchi, J. M. (1994) Adaptive reversion of a frameshift mutation in Escherichia coli by simple base deletions in homopolymeric runs, Science 265, 407–409.
- Frantz, B., Chakrabarty, A. M. (1986) Degradative plasmids in Pseudomonas, in: The Bacteria, vol. 10. The Biology of Pseudomonas ( J. R. Sokatch, Ed.), Orlando, Florida: Academic Press, Inc., 295–323.
- Fujiyama, K., Zhang, Y., Negoro, S., Urabe, I., Okada, H. (1991) Characterization of hybrid enzymes between 6-aminohexanoate-dimer hydrolase and its analogous protein, J. Ferment. Bioeng. 71, 298–302.
- Fukumura, T., Takeuchi, M., Banno, I. (1982) Stepwise loss of metabolism of ɛ-aminocaproic acid cyclic dimer in Alcaligenes species D-2, Eur. J. Appl. Biotechnol. 14, 120–124.
- Gill, D. R., Hartfull, G. F., Salmond, G. P. (1986) A new cell division operon in Escherichia coli, Mol. Gen. Genet. 205, 134–145.
- Hall, B. G., Clarke, N. D. (1977) Regulation of newly evolved enzymes. III. Evolution of ebg repressor during selection for enhanced lactose activity, Genetics, 85, 193–201.
- Harris, R. S., Longerich, S., Rosenberg, S. M. (1994) Recombination in adaptive mutation, Science 264, 258–260.
- Hatanaka, H. S., Fujiyama, K., Negoro, S., Urabe, I., Okada, H. (1991) Alteration of catalytic function of 6-aminohexanoate-dimer hydrolase by site-directed mutagenesis, J. Ferment. Bioeng. 71, 191–193.
- Hiles, I. D., Gallagher, M. P., Jamieson, D. J., Higgins, C. F. (1987) Molecular characterization of the oligopeptide permease of Salmonella typhimurium, J. Mol. Biol. 195, 125–142.
- Holloway, B. W., Morgan, A. F. (1986) Genome organization in Pseudomonas, Annu. Rev. Microbiol. 40, 79–105.
- Hudson, J. A., Crugnola, A. (1987) The in vivo biodegradation of nylon-6 utilized in a particular IUD, J. Biomater. Appl. 1, 487–501.
- Kakudo, S., Negoro, S., Urabe, I., Okada, H. (1993) Nylon oligomer degradation gene, nylC on plasmid pOAD2 from a Flavobacterium strain encodes endo-type 6-aminohexanoate oligomer hydrolase: purification and characterization of the nylC gene product, Appl. Environ. Microbiol. 59, 3978–3980.
- Kakudo, S., Negoro, S., Urabe, I., Okada, H. (1995) Characterization of endotype 6-aminohexanoate-oligomer hydrolase from Flavobacterium sp., J. Ferment. Biol. 80, 12–17.
- Kanagawa, K, Negoro, S., Takada, N., Okada, H. (1989) Plasmid dependence of Pseudomonas sp. strain NK87 enzymes that degrade 6-aminohexanoate-cyclic dimer, J. Bacteriol. 171, 3181–3186.
- Kanagawa, K., Oishi, M., Negoro, S., Urabe, I., Okada, H. (1993) Characterization of the 6-aminohexanoate-dimer hydrolase from Pseudomonas sp. NK87, J. Gen. Microbiol. 139, 787–795.
- Kato, K., Fujiyama, K., Hatanaka, H. S., Prijambada, I. D., Negoro, S., Urabe, I., Okada, H. (1991) Amino acid alterations essential for increasing the catalytic activity of the nylon-oligomer degradation enzyme of Flavobacterium sp., Eur. J. Biochem. 200, 165–169.
- Kato, K., Ohtsuki, K., Mitsuda, H., Yomo, T., Negoro, S., Urabe, I. (1994) Insertion sequence 6100 on plasmid pOAD2, which degrades nylon oligomers, J. Bacteriol. 176, 1197–1200.
- Kato, K., Ohtsuki, K., Koda, Y., Maekawa, T., Yomo, T., Negoro, S., Urabe, I. (1995) A plasmid encoding enzymes for nylon oligomer degradation: nucleotide sequence and analysis of pOAD2, Microbiology 141, 2585–2590.
- Kinoshita, S., Kageyama, S., Iba, K., Yamada, Y., Okada, H. (1975) Utilization of a cyclic dimer and linear oligomers of ɛ-aminocaproic acid by Achromobacter guttatus KI72, Agric. Biol. Chem. 39, 1219–1223.
- Kinoshita, S., Negoro, S., Muramatsu, M., Bisaria, V. S., Sawada, S., Okada, H. (1977) 6-Aminohexanoic acid cyclic dimer hydrolase: a new cyclic amide hydrolase produced by Achromobacter guttatus KI72, Eur. J. Biochem. 80, 489–495.
- Kinoshita, S., Terada, T., Taniguchi, T., Takene, Y., Masuda, S., Matsunaga, N., Okada, H. (1981) Purification and characterization of 6-aminohexanoic acid oligomer hydrolase of Flavobacterium sp. KI72, Eur. J. Biochem. 116, 547–551.
- Kulkarni, R. S., Kanekar, P. P. (1998) Bioremediation of epsilon-caprolactam from nylon-6 waste water by use of Pseudomonas aeruginosa MCM B-407, Curr. Microbiol. 37, 191–194.
- Lenski, R. E., Mittler, J. E. (1993) The directed mutation controversy and Neo-Darwinism, Science 259, 188–194.
- Mori, H., Kondo, A., Ohshima, A., Ogura, T., Hiraga, S. (1986) Structure and function of the F plasmid genes essential for partitioning, J. Mol. Biol. 192, 1–15.
- Negoro, S., Okada, H. (1982) Physical map of nylon oligomer degradative plasmid pOAD2 harbored in Flavobacterium sp. KI72, Agric. Biol. Chem. 46, 745–750.
- Negoro, S., Shinagawa, H., Nakata, A., Kinoshita, S., Hatozaki, T., Okada, H. (1980) Plasmid control of 6-aminohexanoic acid cyclic dimer degradation enzymes of Flavobacterium sp. strain KI72, J. Bacteriol. 143, 238–245.
- Negoro, S., Taniguchi, T., Kanaoka, M., Kimura, H., Okada, H. (1983) Plasmid-determined enzymatic degradation of nylon oligomers, J. Bacteriol. 155, 22–31.
- Negoro, S., Nakamura, S., Kimura, H., Fujiyama, K., Zhang, Y., Kanzaki, N., Okada, H. (1984) Construction of hybrid genes of 6-aminohexanoic acid-oligomer hydrolase and its analogous enzyme: estimation of the intramolecular regions important for the enzyme evolution, J. Biol. Chem. 259, 13648–13651.
- Negoro, S., Mitamura, T., Oka, K., Kanagawa, K., Okada, H. (1989) Determination of the active-site serine of 6-aminohexanoate-dimer hydrolase, Eur. J. Biochem. 185, 521–524.
- Negoro, S., Kakudo, S., Urabe, I., Okada, H. (1992) A new nylon oligomer degradation gene (nylC) on plasmid pOAD2 from Flavobacterium sp., J. Bacteriol. 174, 7948–7953.
- Nomura, N., Deguchi, T., Akutsu, Y. S., Kanbe, T. N., Nakahara, T. (2001) Gene structures and catalytic mechanisms of microbial enzymes able to biodegrade the synthetic solid polymers nylon and polyester polyurethane, Biotechnol. Genet. Eng. Re. 18, 125–147.
- Ohno, S. (1984) Birth of a unique enzyme from an alternative reading frame of the preexisted, internally repetitious coding sequence, Proc. Natl. Acad. Sci. USA 81, 2421–2425.
- Okada, H., Negoro, S., Kimura, H., Nakamura, S. (1983) Evolutionary adaptation of plasmid-encoded enzymes for degrading nylon oligomers, Nature 306, 203–206.
- Okazaki, M., Uemura, T., Nishimori, Y., Wakamatsu, K., Shimosaka, M., Saito, H., Negoro, S., Okada, H. (1988) Analysis of a promoter-like region in Flavobacterium which controls 6-aminohexanoic acid linear oligomer hydrolase gene expression in Escherichia coli, J. Ferment. Technol. 66, 489–494.
- Perego, M., Higgins, C. F., Pearce, S. R., Gallagher, M. P., Hoch, J. A. (1991) The oligopeptide transport system of Bacillus subtilis plays a role in the initiation of sporulation, Molec. Microbiol. 5, 173–185.
- Prijambada, I. D., Negoro, S., Yomo, T., Urabe, I. (1995) Emergence of nylon oligomer degradation enzymes in Pseudomonas aeruginosa PAO through experimental evolution, Appl. Environ. Microbiol. 61, 2020–2022.
- Ramos, J. L., Stolz, A., Reineke, W., Timmis, K. N. (1986) Altered effector specificities in regulators of gene expression: TOL plasmid xylS mutants and their use to engineer expansion of the range of aromatics degraded by bacteria, Proc. Natl. Acad. Sci. USA 83, 8467–8471.
- Rosenberg, S. M., Longerich, S., Gee, P., Harris, R. S. (1994) Adaptive mutation by deletions in small mononucleotide repeats, Science 265, 405–407.
- Rudner, D. Z., LeDeaux, J. R., Ireton, K., Grossman, A. D. (1991) The spo0K locus of Bacillus subtilis is homologous to the oligopeptide permease locus and is required for sporulation and competence, J. Bacteriol. 173, 1388–1398.
- Smith, R., Oliver, C., Williams, D. F. (1987) The enzymatic degradation of polymers in vitro, J. Biomed. Mater. Res. 21, 991–1003.
- Tabata, S., Hooykaas, P. J., Oka, A. (1989) Sequence determination and characterization of the replicator region in the tumor-inducing plasmid pTiB6S3, J. Bacteriol. 171, 1665–1672.
- Thomas, C. M., Smith, C. A. (1986) The trfB region of broad host range plasmid RK2, the nucleotide sequence reveals incC and key regulatory gene trfB/korA/korD as overlapping genes, Nucleic Acids Res. 14, 4453–4469.
- Tobin, M. B., Fleming, M. D., Skatrud, P. L., Miller, J. R. (1990) Molecular characterization of the acyl-coenzyme A: isopenicillin-N acyltransferase gene (penDE) from Penicillium chrysogenum and Aspergillus nidulans and activity of recombinant enzyme in Escherichia coli, J. Bacteriol. 172, 5908–5914.
- Tsuchiya, K., Fukuyama, S., Kanzaki, N., Kanagawa, K., Negoro, S., Okada, H. (1989) High homology between 6-aminohexanoate-cyclic dimer hydrolases of Flavobacterium and Pseudomonas strains, J. Bacteriol. 171, 3187–3191.
- Yomo, T., Urabe, I., Okada, H. (1992) No stop codons in the antisense strands of the genes for nylon oligomer degradation, Proc. Natl. Acad. Sci. USA 89, 3780–3784.
- Zhou, Z. E., Nishimori, Y., Shimosaka, M., Okazaki, M. (1990) Transcription of a gene for 6-aminohexanoic acid linear oligomer hydrolase of Flavobacterium sp. KI72 in Escherichia coli, J. Ferment. Bioeng. 70, 266–268.
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