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Melibiose information


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
CAS Number
  • 585-99-9 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:28053 ☒N
ChEMBL
  • ChEMBL1159652 ☒N
ChemSpider
  • 10974 ☒N
MeSH Melibiose
PubChem CID
  • 11458
UNII
  • 9B1VBE526I checkY
InChI
  • 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
SMILES
  • 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
Chemical formula
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).
☒N verify (what is checkY☒N ?)
Infobox references

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), 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.

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Melibiose

Last Update:

Melibiose is a reducing disaccharide formed by an α-1,6 linkage between galactose and glucose (D-Gal-(α1→6)-D-Glc). It differs from lactose in the chirality...

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Disappearing polymorphs

Last Update:

alpha-melibiose is available. Beta-melibiose is in fact an epimer of alpha-melibiose. However, since when in solution, alpha- and beta-melibiose rapidly...

Word Count : 3372

C12H22O11

Last Update:

Laminaribiose Maltose (malt sugar - cereal) 2α-Mannobiose 3α-Mannobiose Melibiose Melibiulose Nigerose Sophorose Sucrose (table sugar) Trehalose Trehalulose...

Word Count : 87

Melibiulose

Last Update:

Melibiulose is a disaccharide formed from fructose and galactose similar to melibiose. Chemical structure from: Dierk Martin and Frieder W. Lichtenthaler (2006)...

Word Count : 47

Yeast

Last Update:

 cerevisiae secrete an enzyme called melibiase, allowing them to hydrolyse melibiose, a disaccharide, into more fermentable monosaccharides. Top- and bottom-cropping...

Word Count : 9686

Staphylococcus epidermidis

Last Update:

Galactose W D-Glucose + D-Fructose + D-Mannose + Mannitol – N-Acetylglucosamine + Amygdalin + Maltose + D-Melibiose + D-Trehalose + Glycogen + D-Turanose +...

Word Count : 2880

Bacillus subtilis

Last Update:

Galactose + D-Glucose + D-Fructose + D-Mannose + Mannitol + N-Acetylglucosamine + Amygdalin + Maltose + D-Melibiose + D-Trehalose + Glycogen + D-Turanose +...

Word Count : 6259

Bacillus

Last Update:

Galactose + D-Glucose + D-Fructose + D-Mannose + Mannitol + N-Acetylglucosamine + Amygdalin + Maltose + D-Melibiose + D-Trehalose + Glycogen + D-Turanose +...

Word Count : 4338

Membrane protein

Last Update:

Padrós E (August 2013). "The substitution of Arg149 with Cys fixes the melibiose transporter in an inward-open conformation". Biochimica et Biophysica...

Word Count : 1819

Gene nomenclature

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arabinose gal = galactose lac = lactose mal = maltose man = mannose mel = melibiose rha = rhamnose xyl = xylose amp = ampicillin resistance azi = azide resistance...

Word Count : 4143

Vibrio

Last Update:

D-Fructose + V D-Mannose + V Mannitol + V N-Acetylglucosamine + + Amygdalin + – Maltose + + D-Melibiose – – D-Trehalose + – Glycogen + + D-Turanose + +...

Word Count : 2843

Thalassobacillus devorans

Last Update:

D-Fructose, D-Mannose, Mannitol, N-Acetylglucosamine, Amygdalin, Maltose, D-Melibiose, D-Trehalose, Glycogen, D-Turanose. Parte, A.C. "Thalassobacillus". LPSN...

Word Count : 297

Lentilactobacillus kefiri

Last Update:

It is obligately heterofermentive, and can ferment lactose, maltose, melibiose, ribose, as well as sucrose, mannitol and trehalose to a weaker extent...

Word Count : 154

Disaccharide

Last Update:

β(1→6) Mannobiose Two mannoses Either α(1→2), α(1→3), α(1→4), or α(1→6) Melibiose One galactose and one glucose α(1→6) Allolactose One galactose and one...

Word Count : 885

Cronobacter

Last Update:

decarboxylation. Acid is produced from D-glucose, D-sucrose, D-raffinose, D-melibiose, D-cellobiose, D-mannitol, D-mannose, L-rhamnose, L-arabinose, D-trehalose...

Word Count : 1399

University of Birmingham

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confirmed the structures of maltose, cellobiose, lactose, gentiobiose, melibiose, gentianose, raffinose, as well as the glucoside ring tautomeric structure...

Word Count : 14004

Brewing

Last Update:

Technical differences include the ability of lager yeast to metabolize melibiose, and the tendency to settle at the bottom of the fermenter (though ale...

Word Count : 11493

Vibrio natriegens

Last Update:

Galactose + D-Glucose + D-Fructose V D-Mannose V Mannitol V N-Acetylglucosamine + Amygdalin – Maltose + D-Melibiose – D-Trehalose – Glycogen + D-Turanose +...

Word Count : 1151

Salinicola halophilus

Last Update:

Galactose + D-Glucose + D-Fructose + D-Mannose + Mannitol – N-Acetylglucosamine + Amygdalin + Maltose V D-Melibiose + D-Trehalose + Glycogen + D-Turanose +...

Word Count : 198

Yersinia intermedia

Last Update:

intermedia is a Gram-negative species of bacteria which uses rhamnose, melibiose, and raffinose. Its type strain is strain 3953 (=CIP 80-28 =ATCC 29909...

Word Count : 296

Enterococcus casseliflavus

Last Update:

from many sugars, including L-Arabinose, gluconate, inulin, mannitol, melibiose, trehatol, and xylitol. Similar to other members of the genus, E. casseliflavus...

Word Count : 549

Shewanella

Last Update:

Galactose – D-Glucose + D-Fructose + D-Mannose + Mannitol + N-Acetylglucosamine + Amygdalin + Maltose + D-Melibiose + D-Trehalose + Glycogen + D-Turanose +...

Word Count : 1068

Providencia rettgeri

Last Update:

Galactose – D-Glucose + D-Fructose + D-Mannose + Mannitol + N-Acetylglucosamine + Amygdalin + Maltose + D-Melibiose + D-Trehalose + Glycogen + D-Turanose +...

Word Count : 622

Kazachstania yasuniensis

Last Update:

ethylamine hydrochloride, and ethanol. It could not grow on inulin, melibiose, lactose, maltose, melezitose, methyl α- d-glucoside, starch, cellobiose...

Word Count : 509

Bacillus sonorensis

Last Update:

Galactose V D-Glucose V D-Fructose + D-Mannose V Mannitol + N-Acetylglucosamine V Amygdalin V Maltose + D-Melibiose V D-Trehalose + Glycogen + D-Turanose W...

Word Count : 359

Glycoside hydrolase family 27

Last Update:

Alpha-galactosidase (EC 3.2.1.22) (melibiase) catalyzes the hydrolysis of melibiose into galactose and glucose. In man, the deficiency of this enzyme is the...

Word Count : 654

Brachygastra mellifica

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showed 6/7 of the same peaks that appeared in honeybee mesquite honey. Melibiose is the only peak that did not occur in both honeys. Both the glucose and...

Word Count : 1911

Ligilactobacillus animalis

Last Update:

isolates could ferment cellobiose, fructose, glucose, lactose, maltose, melibiose, raffinose, and salicin, but not xylose. The genome size of the type strain...

Word Count : 258

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