Escherichia coli K-12 substr. MG1655 Compound Class: a mono-rhamnolipid

Superclasses: a glycolipida rhamnolipid

This class contains glycosides composed of a single rhamnose moiety joined in an O-glycosidic linkage to a non-glycero lipid moiety. The lipid moiety is mainly two (sometimes one or three) β-hydroxy fatty acid chains (represented here in part by R1 and R2) linked to each other through an ester bond between the β-hydroxyl group of the chain distal to the glycosidic bond with the carboxyl group of the chain proximal to the glycosidic bond. The carboxyl group of the distal chain is usually free, but in a few cases it is esterified with a short alkyl group. The fatty acid chains may be saturated, mono-unsaturated, or poly-unsaturated and the chain length may vary from C8 to C16. In rare cases the rhamnose 2-hydroxyl group distal to the glycosidic bond may be acylated with a long chain alkenoate. [SoberonChavez05, AbdelMawgoud10]. Also see a di-rhamnolipid and a 3-(3-hydroxyalkanoyloxy)alkanoate.

a mono-rhamnolipid compound structure

SMILES: C([R2])C(CC(=O)[O-])OC(=O)CC(C[R1])OC1(C(O)C(O)C(O)C(C)O1)

Created 12-Oct-2010 by Fulcher C, SRI International


AbdelMawgoud10: Abdel-Mawgoud AM, Lepine F, Deziel E (2010). "Rhamnolipids: diversity of structures, microbial origins and roles." Appl Microbiol Biotechnol 86(5);1323-36. PMID: 20336292

Lepine02: Lepine F, Deziel E, Milot S, Villemur R (2002). "Liquid chromatographic/mass spectrometric detection of the 3-(3-hydroxyalkanoyloxy) alkanoic acid precursors of rhamnolipids in Pseudomonas aeruginosa cultures." J Mass Spectrom 37(1);41-6. PMID: 11813309

SoberonChavez05: Soberon-Chavez G, Lepine F, Deziel E (2005). "Production of rhamnolipids by Pseudomonas aeruginosa." Appl Microbiol Biotechnol 68(6);718-25. PMID: 16160828

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Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
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