Title: MeBmt
CAS Registry Number: 59865-23-5
CAS Name: (2S,3R,4R,6E)-3-Hydroxy-4-methyl-2-(methylamino)-6-octenoic acid
Additional Names: (4R)-4-[(E)-2-butenyl]-4,N-dimethyl-L-threonine
Molecular Formula: C10H19NO3
Molecular Weight: 201.26
Percent Composition: C 59.68%, H 9.52%, N 6.96%, O 23.85%
Literature References: Characteristic C9 amino acid of cyclosporins, q.v. Identification in cyclosporin A: A. Ruegger et al., Helv. Chim. Acta 59, 1075 (1976). Syntheses: R. M. Wenger, ibid. 66, 2308 (1983); D. A. Evans, A. E. Weber, J. Am. Chem. Soc. 108, 6757 (1986); U. Schmidt, W. Siegel, Tetrahedron Lett. 28, 2849 (1987). Appears to be necessary for full biological activity of cyclosporin: R. M. Wenger, Angew. Chem. Int. Ed. 24, 77 (1985); D. H. Rich et al., J. Med. Chem. 29, 978 (1986).
Properties: Crystals from ethanol, mp 240-241° (Wenger). [a]D20 +13.5° (c = 0.50 in water, pH 7). Also reported as mp 242-243° (Evans, Weber). [a]D +17° (c = 0.51 in 0.4N aq HCl).
Melting point: mp 240-241° (Wenger); mp 242-243° (Evans, Weber)
Optical Rotation: [a]D20 +13.5° (c = 0.50 in water, pH 7); [a]D +17° (c = 0.51 in 0.4N aq HCl) |