Desosamine

Desosamine
Names
IUPAC name
3,4,6-Trideoxy-3-(dimethylamino)-D-xylo-hexose
Systematic IUPAC name
(2R,3S,5R)-3-(Dimethylamino)-2,5-dihydroxyhexanal
Identifiers
3D model (JSmol)
2412240
ChEBI
ChemSpider
UNII
  • InChI=1S/C8H17NO3/c1-6(11)4-7(9(2)3)8(12)5-10/h5-8,11-12H,4H2,1-3H3/t6-,7+,8+/m1/s1 Y
    Key: VTJCSBJRQLZNHE-CSMHCCOUSA-N Y
  • InChI=1/C8H17NO3/c1-6(11)4-7(9(2)3)8(12)5-10/h5-8,11-12H,4H2,1-3H3/t6-,7+,8+/m1/s1
    Key: VTJCSBJRQLZNHE-CSMHCCOUBT
  • O=C[C@H](O)[C@@H](N(C)C)C[C@H](O)C
Properties
C8H17NO3
Molar mass 175.23 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

Desosamine is a 3-(dimethylamino)-3,4,6-trideoxyhexose found in certain macrolide antibiotics (contain a high level of microbial resistance) such as the commonly prescribed erythromycin, azithromycin, clarithromycin, methymycin, narbomycin, oleandomycin, picromycin and roxithromycin. As the name suggests, these macrolide antibiotics contain a macrolide or lactone ring and they are attached to the ring desosamine which is crucial for bactericidal activity. The biological action of the desosamine-based macrolide antibiotics is to inhibit the bacterial ribosomal protein synthesis. These antibiotics which contain desosamine are widely used to cure bacterial infections in human respiratory system, skin, muscle tissues, and urethra.