Melezitose

Summary

Melezitose, also spelled melicitose, is a nonreducing trisaccharide sugar that is produced by many plant sap eating insects, including aphids such as Cinara pilicornis, by an enzyme reaction. This is beneficial to the insects, as it reduces the stress of osmosis by reducing their own water potential. The melezitose is part of the honeydew which acts as an attractant for ants and also as a food for bees.[1] This is useful to the aphids as they have a symbiotic relationship with ants. Melezitose can be partially hydrolyzed to glucose and turanose the latter of which is an isomer of sucrose.

Melezitose
Names
IUPAC name
α-D-Glucopyranosyl α-D-glucopyranosyl-(1→3)-β-D-fructofuranoside
Systematic IUPAC name
(2R,2′R,3R,3′R,4S,4′S,5S,5′S,6R,6′R)-2,2′-{[(2S,3S,4R,5R)-4-Hydroxy-2,5-bis(hydroxymethyl)oxolane-2,3-diyl]bis(oxy)}bis[6-(hydroxymethyl)oxane-3,4,5-triol]
Other names
Melicitose
Identifiers
  • 597-12-6 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:6731 checkY
ChEMBL
  • ChEMBL386007 checkY
ChemSpider
  • 83787 checkY
ECHA InfoCard 100.008.997 Edit this at Wikidata
  • 92817
UNII
  • T4T25QN29L checkY
  • DTXSID20883458 Edit this at Wikidata
  • InChI=1S/C18H32O16/c19-1-5-8(23)11(26)13(28)16(30-5)32-15-10(25)7(3-21)33-18(15,4-22)34-17-14(29)12(27)9(24)6(2-20)31-17/h5-17,19-29H,1-4H2/t5-,6-,7-,8-,9-,10-,11+,12+,13-,14-,15+,16-,17-,18+/m1/s1 checkY
    Key: QWIZNVHXZXRPDR-WSCXOGSTSA-N checkY
  • InChI=1/C18H32O16/c19-1-5-8(23)11(26)13(28)16(30-5)32-15-10(25)7(3-21)33-18(15,4-22)34-17-14(29)12(27)9(24)6(2-20)31-17/h5-17,19-29H,1-4H2/t5-,6-,7-,8-,9-,10-,11+,12+,13-,14-,15+,16-,17-,18+/m1/s1
    Key: QWIZNVHXZXRPDR-WSCXOGSTBR
  • O1[C@H](CO)[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O[C@@]3(O[C@@H]([C@@H](O)[C@@H]3O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)CO)CO
Properties
C18H32O16
Molar mass 504.438 g·mol−1
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
Honeycomb filled with melezitose

References edit

  1. ^ Fischer, M. K; Shingleton, A. W (2001). "Host plant and ants influence the honeydew sugar composition of aphids". Functional Ecology. 15 (4): 544. doi:10.1046/j.0269-8463.2001.00550.x.