N-Methyl-alpha-L-glucosamine
Title: N-Methyl-a-L-glucosamine
CAS Registry Number: 42852-95-9
CAS Name: 2-(Methylamino)-2-deoxy-a-L-glucopyranose
Molecular Formula: C7H15NO5
Molecular Weight: 193.20
Percent Composition: C 43.52%, H 7.83%, N 7.25%, O 41.41%
Literature References: Together with streptose forms the streptobiosamine moiety of streptomycin: Kuehl et al., J. Am. Chem. Soc. 69, 3032 (1947). Prepn from D-glucose by Streptomyces griseus: Silverman, Rieder, J. Biol. Chem. 235, 1251 (1960); from the antibiotic, bluensomycin: Bannister, Argoudelis, J. Am. Chem. Soc. 85, 34 (1963). Review: Lemieux, Wolfrom, Adv. Carbohydr. Chem. 3, 337 (1948).
Properties: Glass. [a]D25 -62° (c = 1 in methanol).
Optical Rotation: [a]D25 -62° (c = 1 in methanol)
 
Derivative Type: Hydrochloride
Molecular Formula: C7H15NO5.HCl
Molecular Weight: 229.66
Percent Composition: C 36.61%, H 7.02%, N 6.10%, O 34.83%, Cl 15.44%
Properties: Needles from ethanol, mp 160-163°. Freely sol in water. Shows mutarotation. [a]D25 -103° ® -88° (c = 0.6).
Melting point: mp 160-163°
Optical Rotation: [a]D25 -103° ® -88° (c = 0.6)
 
Derivative Type: N-Acetyl deriv
Properties: mp 165-166°. [a]D25 -51° (c = 0.4).
Melting point: mp 165-166°
Optical Rotation: [a]D25 -51° (c = 0.4)
 
Derivative Type: Pentaacetyl deriv
Molecular Formula: C17H25NO10
Molecular Weight: 403.38
Percent Composition: C 50.62%, H 6.25%, N 3.47%, O 39.66%
Properties: mp 160.5-161.5°. [a]D25 -100° (c = 0.7 in chloroform).
Melting point: mp 160.5-161.5°
Optical Rotation: [a]D25 -100° (c = 0.7 in chloroform)

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