D-甘露糖, D-Mannose

Six-carbon carbohydrate. C-2 epimer of glucose and a critical sugar for protein glycosylation. Can be utilized by the brain as an alternative energy source.

D-Mannose is an aldohexose monosaccharide and an epimer of glucose. D-Mannose is found in animals, microbes, and plants, can be used as an energy source by conversion to glucose, and can also be produced from glucose. It is converted via hexokinase to mannose-6-phosphate and then to intermediates that are incorporated into proteins via N-linked glycosylation. It decreases T cell proliferation and increases FoxP3+ T regulatory cells in vitro and prevents diabetes in non-obese diabetic (NOD) mice, a model of autoimmune diabetes, when administered at a dose of 1.1 M in the drinking water. D-Mannose administration during gestation at a dose of 9 mg/ml in the drinking water rescues the embryonic lethal phenotype and prevents deficits in glycosylation in Pmm2R137H/F118L mice, a transgenic model of the congenital glycosylation disorder (CDG) PMM2-CDG, which is characterized by phosphomannomutase 2 (PMM2) gene mutations. Levels of D-mannose are reduced in the serum of patients with PMM2-CDG. Formulations containing D-mannose have been used in the treatment of mannose phosphate isomerase CDG (MPI-CDG).

D-(+)-Mannose analytical standard provided with chromatographic purity, to be used as reference material for qualitative determination.

Aldehydo-D-mannose is the D-enantiomer of aldehydo-mannose. It is a D-mannose and an aldehydo-mannose. It is an enantiomer of an aldehydo-L-mannose.

Mannose, also known as polymannose, belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.

Mannose is under investigation for the basic science of IUGR and Pregnancy.

Title: D-Mannose

CAS Registry Number: 3458-28-4

Additional Names: Seminose; carubinose

Molecular Formula: C6H12O6

Molecular Weight: 180.16

Percent Composition: C 40.00%, H 6.71%, O 53.28%

Literature References: Prepn of a-form by treating ivory nut shavings with H2SO4: Isbell, J. Res. Natl. Bur. Stand. 26, 47 (1941); Isbell, Frush in Methods in Carbohydrate Chemistry, R. L. Whistler, M. L. Wolfrom, Eds. (Academic Press, New York, 1962) pp 145-147. Prepn and stability of a- and b-forms: Reeves, J. Am. Chem. Soc. 72, 1499 (1950); J. Sowden in The Carbohydrates, W. Pigman, Ed. (Academic Press, New York, 1957) pp 94-95.

Derivative Type: a-Form

Properties: Crystals from methanol, mp 133°. [a]D +29.3° ® +14.2° (water).

Melting point: mp 133°

Optical Rotation: [a]D +29.3° ® +14.2° (water)

Derivative Type: b-Form

Properties: Orthorhombic, bisphenoidal needles from alcohol or acetic acid, dec 132°. Sweet taste with bitter aftertaste. d20 1.54. Shows mutarotation. [a]D20 -17.0° ® +14.2° (c = 4). One gram dissolves in 0.4 ml water, 120 ml methanol, 250 ml abs ethanol, 3.5 ml pyridine. pKa (18°): 11.98. Reduces Fehling's soln; is fermented by yeast.

pKa: pKa (18°): 11.98

Optical Rotation: [a]D20 -17.0° ® +14.2° (c = 4)

Density: d20 1.54

Derivative Type: Phenylhydrazone

Molecular Formula: C12H18N2O5

Molecular Weight: 270.28

Percent Composition: C 53.33%, H 6.71%, N 10.36%, O 29.60%

Properties: Crystals from dil ethanol, mp 199-200°. [a]D20 +26.3° ® +33.8° (pyridine).

Melting point: mp 199-200°

Optical Rotation: [a]D20 +26.3° ® +33.8° (pyridine)

Derivative Type: CaCl2-addition compd tetrahydrate

Molecular Formula: C6H12O6.CaCl2.4H2O

Molecular Weight: 363.20

Percent Composition: C 19.84%, H 5.55%, O 44.05%, Ca 11.03%, Cl 19.52%

Properties: mp 101-102°. [a]D20 -31.3° ® +6.0° (c = 9).

Melting point: mp 101-102°

Optical Rotation: [a]D20 -31.3° ® +6.0° (c = 9)

Product name: D-Mannose           CAS: 3458-28-4

M.F.: C₆H₁₂O₆      M.W.: 180.16    Batch No: 20130202     Quantity:12.5kg

    Obt. from the hydrolysates of D-mannans of the tagua palm Phytelephas macrocarpa. Mannans are also present in the ubers of Orchidaceae, seed of Phoenix canariensis, and corms of Amorphophallus konjac (devil’s tongue). They are proliferated by some red algae and yeasts. Mannose is a constit. of blood serum globulins, ovomucoid, and tubercle bacilli. Occurs in trace amounts in apples and peaches. Obt. comly. from ivory nut hydrolysis. Inexpensive starting material for chiral synthesis. pKa1 12.08 (258).

References:

1. Fleet GWJ, Gough MJ, Shing TKM, Tetrahedron Lett. 1984, 25, 4029