8234. Ristocetin

Nomenclature

CAS number: 1404-55-3
Ristomycin; Spontin; Riston.

Description and references

Glycopeptide antibiotic complex produced by the actinomycete Nocardia lurida. Ristocetin A and the more active ristocetin B differ in the number of glucose, mannose, rhamnose and d-arabinose groups in their side chains. Isoln, crystallizn and chemical properties: J. E. Philip et al., Antibiot. Annu. 1956-57, p 699; eidem, US 2990329 (1961 to Abbott). Total structure determn of ristocetin A: D. H. Williams et al., Chem. Commun. 1979, 906; J. R. Kalman, D. H. Williams, J. Am. Chem. Soc. 102, 897 (1980). Identity of ristocetin A with ristomycin A: D. H. Williams et al., J. Chem. Soc. Perkin Trans. 1 1979, 787. 13C-NMR studies: F. Sztaricskai et al., Tetrahedron Lett. 21, 2983 (1980); M. P. Williamson, D. H. Williams, J. Chem. Soc. Perkin Trans. 1 1981, 1483. Revised configuration: C. M. Harris, T. M. Harris, J. Am. Chem. Soc. 104, 363 (1982). Biosynthesis: S. J. Hammond et al., Chem. Commun. 1983, 116. Tool for investigation of platelet aggregation: Howard, Firkin, Thromb. Diath. Haemorrh. 26, 362 (1971). Review: D. C. Jordan, Antibiotics vol. 1, D. Gottlieb, P. Shaw, Eds. (Springer-Verlag, New York, 1967) pp 84-89.

Chemical structure

Derivative

Crystalline sulfates.

Properties

Sol in acidic aq solns; much less sol in the neutral pH range. Generally insol in organic solvents. Both components show good stability in aq acidic solns, but are readily inactivated above pH 7.0. Commercial prepns are mixtures of both with >90% ristocetin A.

Derivative

Ristocetin A.

Nomenclature

CAS number: 11021-66-2
Ristomycin A.
C95H110N8O44; mol wt 2067.92.
C 55.18%, H 5.36%, N 5.42%, O 34.04%.

Properties

Cryst sulfate, [α]D -120 to -133° (water).

Derivative

Ristocetin B.

Nomenclature

CAS number: 1405-59-0
Ristomycin B.
C84H92N8O35; mol wt 1773.66.
C 56.88%, H 5.23%, N 6.32%, O 31.57%.

Properties

Cryst sulfate, [α]D -144 to -149° (water).

Use

Peptide-based probe for platelet aggregation.

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Antibiotics); Polypeptides