Title: Mycosamine
CAS Registry Number: 527-38-8
CAS Name: 3-Amino-3,6-dideoxymannose
Synonyms: 3-amino-3-deoxyrhamnose; 3,6-dideoxy-3-amino-D-mannopyranose; 3-amino-3,6-dideoxy-D-aldohexose
Molecular Formula: C6H13NO4
Molecular Weight: 163.17
Percent Composition: C 44.17%, H 8.03%, N 8.58%, O 39.22%
Literature References: An amino sugar which represents the nitrogen-contg moiety of the antifungal antibiotics, nystatin and amphotericin B,
q.q.v. Isoln and structure: Dutcher
et al., Antibiot. Annu. 1956-1957, 866. Walters
et al., J. Am. Chem. Soc. 79, 5076 (1957); Dutcher
et al., J. Org. Chem. 28, 995 (1963). Stereochemistry: von Saltza
et al., J. Am. Chem. Soc. 83, 2875 (1961);
eidem, J. Org. Chem. 28, 999 (1963).
Derivative Type: N-Acetylmycosamine
Molecular Formula: C8H15NO5
Molecular Weight: 205.21
Percent Composition: C 46.82%, H 7.37%, N 6.83%, O 38.98%
Properties: Needles from methanol + acetone, mp 195-197°. [a]D22 -46° (ethanol).
Melting point: mp 195-197°
Optical Rotation: [a]D22 -46° (ethanol)
Derivative Type: Triacetylmycosamine
Molecular Formula: C12H19NO7
Molecular Weight: 289.28
Percent Composition: C 49.82%, H 6.62%, N 4.84%, O 38.72%
Properties: Prisms from acetone or ethanol, mp 185-187°. [a]D22 +85° (ethanol).
Melting point: mp 185-187°
Optical Rotation: [a]D22 +85° (ethanol)
Derivative Type: Tetraacetylmycosamine
Molecular Formula: C14H21NO8
Molecular Weight: 331.32
Percent Composition: C 50.75%, H 6.39%, N 4.23%, O 38.63%
Properties: Needles from benzene, mp 159-161°. [a]D23 +39.3° (ethanol).
Melting point: mp 159-161°
Optical Rotation: [a]D23 +39.3° (ethanol)
Derivative Type: Hydrochloride
Molecular Formula: C6H13NO4.HCl
Molecular Weight: 199.63
Percent Composition: C 36.10%, H 7.07%, N 7.02%, O 32.06%, Cl 17.76%
Properties: Prismatic rods from ethanol+ ether, mp 162°. [a]D24 -11.5°.
Melting point: mp 162°
Optical Rotation: [a]D24 -11.5°
