6079. N-Methyl-α-l-glucosamine
Nomenclature
CAS number: 42852-95-9
2-(Methylamino)-2-deoxy-α-l-glucopyranose. C7H15NO5; mol wt 193.20.
C 43.52%, H 7.83%, N 7.25%, O 41.41%.
Description and 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. [α]D25 62° (c = 1 in methanol).Derivative
Hydrochloride.C7H15NO5.HCl; mol wt 229.66.
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. [α]D25 103° → 88° (c = 0.6).Derivative
N-Acetyl deriv.Properties
mp 165-166°. [α]D25 51° (c = 0.4).Derivative
Pentaacetyl deriv.C17H25NO10; mol wt 403.38.
C 50.62%, H 6.25%, N 3.47%, O 39.66%.