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)
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 checkY
    Key: VTJCSBJRQLZNHE-CSMHCCOUSA-N checkY
  • 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).
checkY verify (what is checkY☒N ?)

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,[1][2] 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.[3] The biological action of the desosamine-based macrolide antibiotics is to inhibit the bacterial ribosomal protein synthesis.[4] These antibiotics which contain Desosamine are widely used to cure bacterial-causing infections in human respiratory system, skin, muscle tissues, and urethra.

  1. ^ Rodríguez E, Peirú S, Carney JR, Gramajo H (March 2006). "In vivo characterization of the dTDP-D-desosamine pathway of the megalomicin gene cluster from Micromonospora megalomicea". Microbiology. 152 (Pt 3): 667–673. doi:10.1099/mic.0.28680-0. PMID 16514147.
  2. ^ Flickinger MC, Perlman D (April 1975). "Microbial degradation of erythromycins A and B". The Journal of Antibiotics. 28 (4): 307–11. doi:10.7164/antibiotics.28.307. PMID 1150530.
  3. ^ Burgie ES, Holden HM (August 2007). "Molecular architecture of DesI: a key enzyme in the biosynthesis of desosamine". Biochemistry. 46 (31): 8999–9006. doi:10.1021/bi700751d. PMC 2528198. PMID 17630700.
  4. ^ Vázquez-Laslop N, Mankin AS (September 2018). "How Macrolide Antibiotics Work". Trends in Biochemical Sciences. 43 (9): 668–684. doi:10.1016/j.tibs.2018.06.011. PMC 6108949. PMID 30054232.