1724. Calyculin A

Nomenclature

CAS number: 101932-71-2
N-[(3S)-3-[4-[(1E)-3-[(2R,3R,5R,7S,8S,9R)-2-[(1S,3S,4S,5R,6R,7E,9E,11E,13Z)-14-cyano-3,5-dihydroxy-1-methoxy-4,6,8,9,13-pentamethyl-7,9,11,13-tetradecatetraenyl]-9-hydroxy-4,4,8-trimethyl-3-(phosphonooxy)-1,6-dioxaspiro[4.5]dec-7-yl]-1-propenyl]-2-oxazolyl]butyl]-4-deoxy-4-(dimethylamino)-5-O-methyl-l-ribonamide; (-)-calyculin A.
C50H81N4O15P; mol wt 1009.17.
C 59.51%, H 8.09%, N 5.55%, O 23.78%, P 3.07%.

Description and references

One of a family of antitumor marine toxins which inhibits protein phosphatases 1 and 2a. Isoln from the marine sponge, Discodermia calyx, and structure determn: Y. Kato et al., J. Am. Chem. Soc. 108, 2780 (1986); of calyculins B-D: eidem, J. Org. Chem. 53, 3930 (1988); of E-H: S. Matsunaga et al., Tetrahedron 47, 2999 (1991). Revised stereochemistry: S. Matsunaga, N. Fusetani, Tetrahedron Lett. 32, 5605 (1991). Synthesis: N. Tanimoto et al., Angew. Chem. Int. Ed. 33, 673 (1994). Inhibition of protein phosphatases: H. Ishihara et al., Biochem. Biophys. Res. Commun. 159, 871 (1989); selectivity in vivo: B. Favre et al., J. Biol. Chem. 272, 13856 (1997). Binding model: M. K. Lindvall et al., ibid. 23312. Use as inhibitor in biological studies: M. C. Arufe et al., Endocrine 11, 235 (1999); I. Bize et al., Am. J. Physiol. 277, C926 (1999).

Chemical structure

Properties

Colorless needles from a mixture of hexane, ether and acetone, mp 247-249°. [α]D -60° (c = 0.1 in ethanol). uv max (ethanol): 230, 342 nm (ε 12000, 19000).

Use

Inhibitor of phosphatases 1 and 2a.