Neamine
Title: Neamine
CAS Registry Number: 3947-65-7
CAS Name: 2-Deoxy-4-O-(2,6-diamino-2,6-dideoxy-a-D-glucopyranosyl)-D-streptamine
Additional Names: neomycin A
Molecular Formula: C12H26N4O6
Molecular Weight: 322.36
Percent Composition: C 44.71%, H 8.13%, N 17.38%, O 29.78%
Literature References: Component of the antibiotic complex neomycin, q.v. Isoln: Dutcher et al., J. Am. Chem. Soc. 73, 1384 (1951). Identity of neomycin A and neamine: Leach, Teeters, ibid. 74, 3187 (1952). Prepn from neomycin B: Peck et al., US 2691675 (1954 to Merck & Co.). Structure: Carter et al., J. Am. Chem. Soc. 83, 3723 (1961); Hichens, Rinehart, ibid. 85, 1547 (1963). Synthesis: Umezawa et al., J. Antibiot. 20A, 53 (1967); H. Kohno et al., Agric. Biol. Chem. 39, 1091 (1975); A. Harayama et al., Bull. Chem. Soc. Jpn. 52, 3626 (1979).
Properties: Crystals from water or aq alc, dec 225-226°, [a]D25+112.8° (c = 1). IR spectrum: Leach, Teeters, J. Am. Chem. Soc. 73, 2794 (1951).
Optical Rotation: [a]D25+112.8° (c = 1)
 
Derivative Type: Hydrochloride
Molecular Formula: C12H26N4O6.4HCl
Molecular Weight: 468.20
Percent Composition: C 30.78%, H 6.46%, N 11.97%, O 20.50%, Cl 30.29%
Properties: Amorphous, dec 250-260°, [a]D25+83° (c = 1).
Optical Rotation: [a]D25+83° (c = 1)
 
Derivative Type: N-Acetyl deriv
Molecular Formula: C12H26N4O6.(CH3CO)4
Molecular Weight: 494.54
Percent Composition: C 48.57%, H 7.74%, N 11.33%, O 32.35%
Properties: Crystals from methanol, mp 334-336°. [a]D25 +87° (c = 1).
Melting point: mp 334-336°
Optical Rotation: [a]D25 +87° (c = 1)

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