Title: Hypoglycine A
CAS Registry Number: 156-56-9
CAS Name: (aS,1R)-a-Amino-2-methylenecyclopropanepropanoic acid
Additional Names: 2-methylenecyclopropanealanine; 2-amino-4,5-methylenehex-5-enoic acid; a-amino-b-(2-methylenecyclopropyl)propionic acid; hypoglycin; hypoglycin A
Molecular Formula: C7H11NO2
Molecular Weight: 141.17
Percent Composition: C 59.56%, H 7.85%, N 9.92%, O 22.67%
Literature References: Hypoglycemic principle from the akee plant, Blighia sapida Kon., Sapindaceae: Hassall et al., Nature 173, 356 (1954); Hassall, Reyle, Biochem. J. 60, 334 (1955). Structure: de Ropp et al., J. Am. Chem. Soc. 80, 1004 (1958); Renner et al., Helv. Chim. Acta 41, 589 (1958); Ellington et al., J. Chem. Soc. 1959, 80. Synthesis: Carbon et al., J. Am. Chem. Soc. 80, 1002 (1958); Black, Landor, Tetrahedron Lett. 1963, 1065.
Properties: Yellow plates from methanol + water, mp 280-284°. [a]D32 +9.2°.
Melting point: mp 280-284°
Optical Rotation: [a]D32 +9.2°
Derivative Type: Methyl ester hydrochloride
Molecular Formula: C8H13NO2.HCl
Molecular Weight: 191.66
Percent Composition: C 50.13%, H 7.36%, N 7.31%, O 16.70%, Cl 18.50%
Properties: Needles from methanol + ether, mp 151-152°. [a]D22 +36° (c = 2.0).
Melting point: mp 151-152°
Optical Rotation: [a]D22 +36° (c = 2.0)
Derivative Type: Hypoglycine B
CAS Registry Number: 502-37-4
CAS Name: N-L-g-Glutamyl-3-(2-methylenecyclopropyl)alanine
Additional Names: g-L-glutamylhypoglycine
Molecular Formula: C12H18N2O5
Molecular Weight: 270.28
Percent Composition: C 53.33%, H 6.71%, N 10.36%, O 29.60%
Literature References: Structure: Jöhl, Stoll, Helv. Chim. Acta 42, 156 (1959); Hassall, John, J. Chem. Soc. 1960, 4112. Synthesis: Jöhl, Stoll, Helv. Chim. Acta 42, 716 (1959).
Properties: Yellow needles from acetone + water, mp 194-195°, 200-206°. [a]D32 +9.6° (c = 1.12). Neutralization equivalent 175.
Melting point: mp 194-195°, 200-206°
Optical Rotation: [a]D32 +9.6° (c = 1.12)
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