Desosamine

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Desosamine

IUPAC name (2R,3S,5R)-3-Dimethylamino-2,5-dihydroxyhexanal
Identifiers
CAS number	5779-39-5^Y
PubChem	168997
ChemSpider	147813^Y
ChEBI	CHEBI:32540^Y
Jmol-3D images	{{#if:O=C[C@H](O)[C@@H](N(C)C)C[C@H](O)C\|Image 1
SMILES O=C[C@H](O)[C@@H](N(C)C)C[C@H](O)C
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^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
Properties
Molecular formula	C₈H₁₇NO₃
Molar mass	175.23 g/mol
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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]

↑ 1.0 1.1 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.
↑ Flickinger MC, Perlman D (April 1975). "Microbial degradation of erythromycins A and B". J. Antibiot. 28 (4): 307–11. PMID 1150530.

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