Chloropeptin

Discovery, producing organism and structure (1-4)

During screening for new gp120-CD4 binding inhibitors from microorganisms, chloropeptins I and II were isolated from the culture broth of the actinomycete strain WK-3419. While the major component, chloropeptin I, was identified as a novel compound, chloropeptin II was identified as complestatin (5,6).

The planer structure of chloropeptin I was elucidated by NMR analysis (1,4). The stereostructure was elucidated by NOE experiments in combination with molecular dynamics conformation analysis and Monte Carlo calculations (2).

Physical data (Chloropeptin I)

Pale yellow brown powder. C₆₁H₄₅N₇O₁₅C_l6; mol wt 1328.79. Sol. in DMSO, MeOH, alkaline H₂O, pyridine. Insol. in H₂O, acetone, CHC_l3.

Biological activity (1,4,7)

1) Inhibition of gp120-CD4 binding

2) Inhibition of HIV replication in the viral core protein level

3) Anti-HIV-1 activities of chloropeptin I, complestatin, dextran sulfate, and AZT

4) Antimicrobial activity of chloropeptin I and complestatin assayed using paper discs

References

1. [553] K. Matsuzaki et al., J. Antibiot., 47, 1173–1174 (1994)
2. [649] H. Gouda et al., J. Am. Chem. Soc., 118, 13087–13088 (1996)
3. [652] K. Matsuzaki et al., J. Antibiot., 50, 66–69 (1997)
4. [664] H. Tanaka et al., Nippon Nogei Kagaku Kaishi, 71, 530–534 (1997)
5. I. Kaneko et al., J. Antibiot., 42, 236–241 (1989)
6. H. Seto et al., Tetrahedron Lett., 30, 4987–4990 (1989)
7. [651] H. Tanaka et al., J. Antibiot., 50, 58–65 (1997)