Desosamine

Desosamine

Names
IUPAC name (2R,3S,5R)-3-Dimethylamino-2,5-dihydroxyhexanal
Identifiers
CAS Number	5779-39-5
3D model (Jmol)	Interactive image
ChEBI	CHEBI:32540
ChemSpider	147813
PubChem	168997
InChI 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 Key: VTJCSBJRQLZNHE-CSMHCCOUSA-N 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
SMILES O=C[C@H](O)[C@@H](N(C)C)C[C@H](O)C
Properties
Chemical formula	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).
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Infobox references

Desosamine is a 3-(dimethylamino)-3,4,6-trideoxyhexose found in certain macrolide antibiotics such as the commonly prescribed erythromycin.^[1][2]

Biosynthesis

Six enzymes are required for its biosynthesis from TDP-glucose in Streptomyces venezuelae.^[1]

References

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 (Reading, Engl.). 152 (Pt 3): 667–73. doi:10.1099/mic.0.28680-0. PMID 16514147.
2. Flickinger MC, Perlman D (April 1975). "Microbial degradation of erythromycins A and B". J. Antibiot. 28 (4): 307–11. doi:10.7164/antibiotics.28.307. PMID 1150530.