Desosamine

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, clarithroymcin, 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-causing infections in human respiratory system, skin, muscle tissues, and urethra.

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)
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
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