Ristocetin
Title: Ristocetin
CAS Registry Number: 1404-55-3
Trademarks: Ristomycin; Spontin; Riston
Literature 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.
 
Derivative Type: 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 Type: Ristocetin A
CAS Registry Number: 11021-66-2
Additional Names: Ristomycin A
Molecular Formula: C95H110N8O44
Molecular Weight: 2067.92
Percent Composition: C 55.18%, H 5.36%, N 5.42%, O 34.04%
Properties: Cryst sulfate, [a]D -120 to -133° (water).
Optical Rotation: [a]D -120 to -133° (water)
 
Derivative Type: Ristocetin B
CAS Registry Number: 1405-59-0
Additional Names: Ristomycin B
Molecular Formula: C84H92N8O35
Molecular Weight: 1773.66
Percent Composition: C 56.88%, H 5.23%, N 6.32%, O 31.57%
Properties: Cryst sulfate, [a]D -144 to -149° (water).
Optical Rotation: [a]D -144 to -149° (water)
 
Use: Peptide-based probe for platelet aggregation.
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); Polypeptides.

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