Rhamnolipid

Rhamnolipid

Rhamnolipid 1, an example of a di-rhamnolipid
Names
IUPAC name
3-[3-[(2R,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxydecanoyloxy]decanoic acid
Other names
3-[(3-{[6-deoxy-2-O-(6-deoxy-alpha-L-mannopyranosyl)-alpha-L-mannopyranosyl]oxy}decanoyl)oxy]decanoic acid
Identifiers
3D model (JSmol)
UNII
  • InChI=1S/C32H58O13/c1-5-7-9-11-13-15-21(17-23(33)34)43-24(35)18-22(16-

    14-12-10-8-6-2)44-32-30(28(39)26(37)20(4)42-32)45-31-29(40)27(38)25(36) 19(3)41-31/h19-22,25-32,36-40H,5-18H2,1-4H3,(H,33,34)/t19-,20-,21?,22?,

    25-,26-,27+,28+,29+,30+,31-,32-/m0/s1
  • CCCCCCCC(CC(=O)O)OC(=O)CC(CCCCCCC)OC1C(C(C(C(O1)C)O)O)OC2C(C(C(C(O2)C)O)O)O
Properties
C32H58O13
Molar mass 650.79512
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Rhamnolipids are a class of glycolipid produced by Pseudomonas aeruginosa, amongst other organisms, frequently cited as bacterial surfactants.[1][2][3] They have a glycosyl head group, in this case a rhamnose moiety, and a 3-(hydroxyalkanoyloxy)alkanoic acid (HAA) fatty acid tail, such as 3-hydroxydecanoic acid.[4][5]

Specifically there are two main classes of rhamnolipids: mono-rhamnolipids and di-rhamnolipids, which consist of one or two rhamnose groups respectively.[6] Rhamnolipids are also heterogeneous in the length and degree of branching of the HAA moiety,[1] which varies with the growth media used and the environmental conditions.[7]

  1. ^ a b Desai JD, Banat IM (March 1997). "Microbial production of surfactants and their commercial potential". Microbiol. Mol. Biol. Rev. 61 (1): 47–64. doi:10.1128/AEM.01737-15. PMC 232600. PMID 9106364.
  2. ^ Lang S, Wullbrandt D (January 1999). "Rhamnose lipids--biosynthesis, microbial production and application potential". Appl. Microbiol. Biotechnol. 51 (1): 22–32. doi:10.1007/s002530051358. PMID 10077819.
  3. ^ Soberón-Chávez G, Aguirre-Ramírez M, Sánchez R (December 2005). "The Pseudomonas aeruginosa RhlA enzyme is involved in rhamnolipid and polyhydroxyalkanoate production". J. Ind. Microbiol. Biotechnol. 32 (11–12): 675–7. doi:10.1007/s10295-005-0243-0. PMID 15937697.
  4. ^ Ochsner UA, Fiechter A, Reiser J (August 1994). "Isolation, characterization, and expression in Escherichia coli of the Pseudomonas aeruginosa rhlAB genes encoding a rhamnosyltransferase involved in rhamnolipid biosurfactant synthesis". J. Biol. Chem. 269 (31): 19787–95. doi:10.1016/S0021-9258(17)32089-6. PMID 8051059.
  5. ^ Cabrera-Valladares N, Richardson AP, Olvera C, Treviño LG, Déziel E, Lépine F, Soberón-Chávez G (November 2006). "Monorhamnolipids and 3-(3-hydroxyalkanoyloxy)alkanoic acids (HAAs) production using Escherichia coli as a heterologous host". Appl. Microbiol. Biotechnol. 73 (1): 187–94. doi:10.1007/s00253-006-0468-5. PMID 16847602.
  6. ^ Rahim R, Ochsner UA, Olvera C, Graninger M, Messner P, Lam JS, Soberón-Chávez G (May 2001). "Cloning and functional characterization of the Pseudomonas aeruginosa rhlC gene that encodes rhamnosyltransferase 2, an enzyme responsible for di-rhamnolipid biosynthesis". Mol. Microbiol. 40 (3): 708–18. doi:10.1046/j.1365-2958.2001.02420.x. PMID 11359576.
  7. ^ Mulligan CN (January 2005). "Environmental applications for biosurfactants". Environ. Pollut. 133 (2): 183–98. Bibcode:2005EPoll.133..183M. doi:10.1016/j.envpol.2004.06.009. PMID 15519450.