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Cyanopeptolins, new depsipeptides from the cyanobacterium Microcystis sp. pcc 7806.
Open accessAbstract
Four depsipeptides (peptide lactones), called cyanopeptolins A, B, C and D, have been isolated from the cyanobacterium Microcystis sp. PCC 7806. They possess identical structures consisting of cyclic L-glutamic acid-gamma-aldehyde, L-leucine, N-methyl-phenylalanine, L-valine, L-threonine, L-aspartic acid, hexanoic acid and a variable basic amino acid. This variable amino acid can be L-arginine (cyanopeptolin A), L-lysine (cyanopeptolin B), N epsilon-methyl-L-lysine (cyanopeptolin C) and N epsilon,N epsilon-dimethyl-L-lysine (cyanopeptolin D), respectively. The L-glutamic acid-gamma-aldehyde and the amino group of L-leucine form an unusual 3-amino-6-hydroxy-2-oxo-1-piperidine system. L-Threonine is connected to L-valine via its hydroxy-group forming an ester bonding. The hexanoic acid residue is attached to the N-terminal aspartic acid residue which is not a part of the ring structure. The isolation procedure of the four cyanopeptolins as well as structure elucidation are described. Amino acid analysis, GC/MS analysis, FAB-MS and several NMR techniques were used to reveal the structures.
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Cites
Generic Assignments, Strain Histories and Properties of Pure Cultures of Cyanobacteria
Rippka, R., Stanier, R. Y., Deruelles, J., Herdman, M., & Waterbury, J. B. (1979) · Microbiology · doi:10.1099/00221287-111-1-1 · Cited by 7,606
Cited by
Dittmann, E., Neilan, B. A., Erhard, M., Von Döhren, H., & Börner, T. (1997) · Molecular Microbiology · doi:10.1046/j.1365-2958.1997.6131982.x · Cited by 395
Bioactive compounds produced by cyanobacteria
Namikoshi, M., & Rinehart, K. (1996) · Journal of Industrial Microbiology & Biotechnology · doi:10.1007/bf01574768 · Cited by 356
Cyclic peptides and depsipeptides from cyanobacteria: A review
Moore, R. E. (1996) · Journal of Industrial Microbiology · doi:10.1007/bf01570074 · Cited by 277
Frangeul, L., Quillardet, P., Castets, A.-M., Humbert, J.-F., Matthijs, H. C., Cortez, D., Tolonen, A., Zhang, C.-C., Gribaldo, S., Kehr, J.-C., et al. (2008) · BMC Genomics · doi:10.1186/1471-2164-9-274 · Cited by 221
Murakami, M., Ishida, K., Okino, T., Okita, Y., Matsuda, H., & Yamaguchi, K. (1995) · Tetrahedron Letters · doi:10.1016/0040-4039(95)00396-t · Cited by 150
Metadata
- Authors
- MARTIN, C., OBERER, L., INO, T., KÖNIG, W. A., BUSCH, M., & WECKESSER, J.
- Venue
- The Journal of Antibiotics
- Published
- 1993
- Volume
- 46
- Issue
- 10
- Pages
- 1550-1556
- ISSN
- 0021-8820 (ISSN-L)
- 1881-1469
- OpenAlex
- W1982821639
- Cited by
- 162
- References
- 1
- FWCI
- 5.42
- Type
- journal article
- Language
- en
- Open access
- bronze
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- The paper
- MARTIN, C., OBERER, L., INO, T., KÖNIG, W. A., BUSCH, M., & WECKESSER, J. (1993). Cyanopeptolins, new depsipeptides from the cyanobacterium Microcystis sp. pcc 7806. The Journal of Antibiotics. https://doi.org/10.7164/antibiotics.46.1550
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