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MetaCyc Compound Class: maltose

Synonyms: α-D-glucopyranose-(1→4)-D-glucopyranose, maltose

Superclasses: all carbohydrates a carbohydrate a glycan an oligosaccharide a disaccharide
all carbohydrates a carbohydrate a glycan an oligosaccharide a malto-oligosaccharide a linear malto-oligosaccharide

Summary:
Maltose is composed of two glucose molecules linked by an α 1,4-glycosidic linkage. Maltose is produced by the hydrolysis of starch and similar compounds, and can be hydrolyzed to glucose by the enzyme maltase.

Chemical Formula: C12H22O11

Instances:
α-maltose ,
β-maltose

Citations: [Stryer88]

Molecular Weight: 342.3 Daltons

Monoisotopic Molecular Weight: 342.11621154930003 Daltons

SMILES: C(C1(OC(C(C(C1O)O)O)OC2(C(OC(C(C2O)O)O)CO)))O

InChI: InChI=1S/C12H22O11/c13-1-3-5(15)6(16)9(19)12(22-3)23-10-4(2-14)21-11(20)8(18)7(10)17/h3-20H,1-2H2/t3-,4-,5-,6+,7-,8-,9-,10-,11?,12-/m1/s1

Unification Links: CAS:69-79-4 , ChEBI:17306 , ChemSpider:6019

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -150.79538 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

glycogen degradation I :
maltotetraose + D-glucopyranose ← maltotriose + maltose

starch degradation I :
a linear malto-oligosaccharide [(glucose)n] + H2O → a linear malto-oligosaccharide [(glucose)n-2] + maltose
maltose + H2O → β-D-glucose + α-D-glucose

starch degradation II :
a linear malto-oligosaccharide [(glucose)n] + H2O → a linear malto-oligosaccharide [(glucose)n-2] + maltose

starch degradation V :
a maltodextrin(n+1) + α-D-glucose ← a maltodextrin(n) + maltose

sucrose biosynthesis II :
SHG-glucosyln+1 + β-D-glucose ← SHG-glucosyln + maltose

Not in pathways:
maltose + H2O → 2 glucose

Reactions known to produce the compound:

glycogen degradation I :
maltotriose + H2O → maltose + D-glucopyranose

starch degradation II :
an exposed unphosphorylated, unbranched malto-oligosaccharide tail on amylopectin[chloroplast stroma] + n H2O[chloroplast stroma]maltose[chloroplast stroma] + an exposed unphosphorylated, (α-1,6)-branched malto-oligosaccharide tail on amylopectin[chloroplast stroma]
an exposed unphosphorylated, unbranched malto-oligosaccharide tail on amylopectin[chloroplast stroma] + n H2O[chloroplast stroma] → amylopectin[chloroplast stroma] + maltose[chloroplast stroma]

starch degradation IV :
a maltodextrin + H2O → maltose + α-D-glucose

starch degradation V :
starch[extracellular space] + H2O[extracellular space] → a maltodextrin(n)[extracellular space] + maltose[extracellular space] + D-glucopyranose[extracellular space]

Not in pathways:
a 1,4-α-D-glucan + H2O → a 1,4-α-D-glucan + maltose
starch + H2O → maltose + glucose
(1,6-α-D-glucosyl)(m+1) + H2O → (1,6-α-D-glucosyl)(m-1) + maltose
α-maltose 6'-phosphate + H2O → maltose + phosphate

starch degradation I :
a long-linear glucan + n H2O → a linear malto-oligosaccharide

starch degradation II :
an exposed unphosphorylated, (α-1,6)-branched malto-oligosaccharide tail on amylopectin[chloroplast stroma] + n H2O[chloroplast stroma] → amylopectin[chloroplast stroma] + n a linear malto-oligosaccharide[chloroplast stroma]

starch biosynthesis :
n a (1,6)-α-D-glucosyl-(1,4)-α-glucan highly branched[chloroplast stroma] + n H2O[chloroplast stroma] → n a malto-oligosaccharide[chloroplast stroma] + n (1,6)-α-D-glucosyl-(1,4)-α-glucan moderately branched[chloroplast stroma]


keratan sulfate + H2O → n an oligosaccharide
blood group substance B + H2O → n an oligosaccharide
blood group substance A + H2O → n an oligosaccharide
a polysaccharide + H2O → an oligosaccharide
a sialyloligosaccharide + H2O → an oligosaccharide + N-acetylneuraminate
a 1,2-β-D-glucan + H2O → n an oligosaccharide
a fucoidan + H2O → fucose + a fucose sulfate + an oligosaccharide


an N-acetyl-β-D-galactosalaminyl-[glycan] + H2O → a glycan + N-acetyl-β-D-galactosamine

Reactions known to both consume and produce the compound:

maltose degradation :
maltose + phosphate ↔ β-D-glucose 1-phosphate + β-D-glucose

trehalose biosynthesis IV :
maltose ↔ α,α-trehalose

Not in pathways:
maltose + acetyl-CoA ↔ acetylmaltose + coenzyme A

In Reactions of unknown directionality:

Not in pathways:
maltohexaose + β-D-glucose = maltopentaose + maltose
maltopentaose + D-glucopyranose = maltotetraose + maltose
2 α-D-glucose 1-phosphate + H2O = maltose + 2 phosphate
maltose + H2O = 2 β-D-glucose
maltohexaose + maltose = maltoheptaose + β-D-glucose


a linear malto-oligosaccharide [(glucose)n] + phosphate = α-D-glucose 1-phosphate + a linear malto-oligosaccharide [(glucose)n-1]

In Transport reactions:
maltose[chloroplast stroma]maltose[cytosol] ,
maltose[cco-cytosol-cco-chlor-str]maltose[cco-cytosol-cco-chlor-str] ,
maltose[extracellular space] + ATP + H2O → maltose[cytosol] + ADP + phosphate + H+ ,
maltose[extracellular space] + H+[extracellular space]maltose[cytosol] + H+[cytosol] ,
maltose[extracellular space]maltose[periplasmic space] ,
maltose[periplasmic space] + ATP + H2O → maltose[cytosol] + ADP + phosphate + H+ ,
maltose[periplasmic space]maltose[cytosol] ,
a [PTS enzyme I]-Nπ-phospho-L-histidine + maltose[out] → maltose 6'-phosphate[in] + a [PTS enzyme I]-L-histidine ,
an oligosaccharide[extracellular space] + ATP + H2O ↔ an oligosaccharide[cytosol] + ADP + phosphate

Enzymes inhibited by maltose, sorted by the type of inhibition, are:

Inhibitor (Mechanism unknown) of: sucrose transporter [Sauer94] , sucrose transporter [Sauer94] , UDP-α-D-glucose:glucosyl-glycogenin α-D-glucosyltransferase [Cao93] , UDP-α-D-glucose:glycogenin α-D-glucosyltransferase [Cao93]

Credits:
Created 29-Sep-2012 by Caspi R , SRI International


References

Cao93: Cao Y, Mahrenholz AM, DePaoli-Roach AA, Roach PJ (1993). "Characterization of rabbit skeletal muscle glycogenin. Tyrosine 194 is essential for function." J Biol Chem 268(20);14687-93. PMID: 8325847

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Sauer94: Sauer N, Stolz J (1994). "SUC1 and SUC2: two sucrose transporters from Arabidopsis thaliana; expression and characterization in baker's yeast and identification of the histidine-tagged protein." Plant J 6(1);67-77. PMID: 7920705

Stryer88: Stryer L "Biochemistry." WH Freeman and Co., 3rd edition, New York, 1988.


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Fri Nov 21, 2014, biocyc14.