Melibiose

Melibiose
Names
IUPAC name
6-O-α-D-Galactopyranosyl-β-D-glucopyranose
Systematic IUPAC name
(2R,3R,4S,5S,6R)-6-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxane-2,3,4,5-tetrol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
MeSH Melibiose
UNII
  • InChI=1S/C12H22O11/c13-1-3-5(14)8(17)10(19)12(23-3)21-2-4-6(15)7(16)9(18)11(20)22-4/h3-20H,1-2H2/t3-,4-,5+,6-,7+,8+,9-,10-,11-,12+/m1/s1
    Key: DLRVVLDZNNYCBX-ZZFZYMBESA-N
  • C([C@@H]1[C@@H]([C@@H]([C@H]([C@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)O)O)O)O)O)O)O)O
Properties
C12H22O11
Molar mass 342.297 g·mol−1
Melting point 84–85 °C (183–185 °F; 357–358 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Melibiose is a reducing disaccharide formed by an α-1,6 linkage between galactose and glucose (D-Gal-(α1→6)-D-Glc).[1][2] It differs from lactose in the chirality of the carbon where the galactose ring is closed and that the galactose is linked to a different point on the glucose moiety. It can be formed by invertase-mediated hydrolysis of raffinose, which produces melibiose and fructose. Melibiose can be broken down into its component saccharides, glucose and galactose, by the enzyme alpha-galactosidase, such as MEL1 from Saccharomyces pastorianus (lager yeast).

Melibiose cannot be used by Saccharomyces cerevisiae[3] (ale yeast), so this is one test to differentiate between the two yeast species.

  1. ^ Thisbe K. Lindhorst (2007). Essentials of Carbohydrate Chemistry and Biochemistry (1 ed.). Wiley-VCH. ISBN 978-3527315284.
  2. ^ John F. Robyt (1997). Essentials of Carbohydrate Chemistry (1 ed.). Springer. ISBN 0387949518.
  3. ^ Bokulicha. Nicholas A. & Bamforth. Charles W. (1 June 2013). "The Microbiology of Malting and Brewing". American Society for Microbiology. pp. 157–172. Retrieved 2 May 2015.