alpha-maltose (CHEBI:18167)

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CHEBI:18167 - α-maltose

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ChEBI Name	α-maltose

ChEBI ID	CHEBI:18167

ChEBI ASCII Name	alpha-maltose

Definition	A maltose that has α-configuration at the reducing end anomeric centre.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:43893, CHEBI:10300, CHEBI:12340, CHEBI:22463

Supplier Information	ChemicalBook:CB9965724, eMolecules:475543, ZINC000004095490

Download	Molfile XML SDF

more structures >>

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reading 45 atoms

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45 atoms created

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Molfile expand

Wikipedia	License
Maltose ( or ), also known as maltobiose or malt sugar, is a disaccharide formed from two units of glucose joined with an α(1→4) bond. In the isomer isomaltose, the two glucose molecules are joined with an α(1→6) bond. Maltose is the two-unit member of the amylose homologous series, the key structural motif of starch. When beta-amylase breaks down starch, it removes two glucose units at a time, producing maltose. An example of this reaction is found in germinating seeds, which is why it was named after malt. Unlike sucrose, it is a reducing sugar.
Read full article at Wikipedia

Formula

C12H22O11

Net Charge

Average Mass

342.29648

Monoisotopic Mass

342.11621

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

InChIKey

GUBGYTABKSRVRQ-ASMJPISFSA-N

SMILES

OC[C@H]1O[C@H](O[C@@H]2[C@@H](CO)O[C@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O

Roles Classification
Biological Role(s):	Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. (via maltose ) Saccharomyces cerevisiae metabolite Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ). (via maltose ) human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). (via maltose ) mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). (via maltose ) sweetening agent Substance that sweeten food, beverages, medications, etc. (via maltose )

Application(s):	sweetening agent Substance that sweeten food, beverages, medications, etc. (via maltose )

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	α-maltose (CHEBI:18167) is a maltose (CHEBI:17306)

Incoming	α-D-Glcp-(1→3)-[α-D-Glcp-(1→4)]-α-D-Glcp (CHEBI:148042) has functional parent α-maltose (CHEBI:18167) α-D-Glcp-(1→4)-α-D-Glcp-(1→3)-D-Glcp (CHEBI:146798) has functional parent α-maltose (CHEBI:18167) 1-O-acetyl-α-maltose (CHEBI:2411) has functional parent α-maltose (CHEBI:18167)

IUPAC Name

α-D-glucopyranosyl-(1→4)-α-D-glucopyranose

Synonyms	Sources
4-O-alpha-D-glucopyranosyl-alpha-D-glucopyranose	PDBeChem
4-O-α-D-glucopyranosyl-α-D-glucopyranose	ChEBI
4-O-α-D-glucopyranosyl-α-D-glucopyranose	IUPAC
α-D-Glcp-(1→4)-α-D-Glcp	IUPAC
alpha-Malt sugar	KEGG COMPOUND
alpha-Maltose	KEGG COMPOUND
α-maltose	UniProt
Glca1-4Glca	ChEBI
Glcα1-4Glca	ChEBI
Glcα1-4Glcα	ChEBI
MALTOSE	PDBeChem

Manual Xrefs	Databases
ALPHA-MALTOSE	MetaCyc
C00897	KEGG COMPOUND
HMDB0000163	HMDB
MAL	PDBeChem
Maltose	Wikipedia
View more database links

Registry Numbers	Types	Sources
1292753	Reaxys Registry Number	Reaxys
1485260	Gmelin Registry Number	Gmelin
4482-75-1	CAS Registry Number	KEGG COMPOUND

Citations

Jandus P, Boligan KF, Smith DF, de Graauw E, Grimbacher B, Jandus C, Abdelhafez MM, Despont A, Bovin N, Simon D, Rieben R, Simon HU, Cummings RD, von Gunten S (2019)
The architecture of the IgG anti-carbohydrate repertoire in primary antibody deficiencies.
Blood 134, 1941-1950 [PubMed:31537530]
[show Abstract]

Schneider C, Smith DF, Cummings RD, Boligan KF, Hamilton RG, Bochner BS, Miescher S, Simon HU, Pashov A, Vassilev T, von Gunten S (2015)
The human IgG anti-carbohydrate repertoire exhibits a universal architecture and contains specificity for microbial attachment sites.
Science translational medicine 7, 269ra1 [PubMed:25568069]
[show Abstract]

von Gunten S, Smith DF, Cummings RD, Riedel S, Miescher S, Schaub A, Hamilton RG, Bochner BS (2009)
Intravenous immunoglobulin contains a broad repertoire of anticarbohydrate antibodies that is not restricted to the IgG2 subclass.
The Journal of allergy and clinical immunology 123, 1268-76.e15 [PubMed:19443021]
[show Abstract]

Schnupf U, Willett JL, Bosma WB, Momany FA (2007)
DFT studies of the disaccharide, alpha-maltose: relaxed isopotential maps.
Carbohydrate research 342, 2270-2285 [PubMed:17669381]
[show Abstract]

Last Modified

27 June 2023

ChEBI

CHEBI:18167 - α-maltose

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