Page last updated: 2024-10-24

oligo-1,6-glucosidase activity

Definition

Target type: molecularfunction

Catalysis of the hydrolysis of (1->6)-alpha-D-glucosidic linkages in some oligosaccharides produced from starch and glycogen by alpha-amylase, and in isomaltose. Releases a free alpha-D-glucose. [EC:3.2.1.10]

Oligo-1,6-glucosidase activity is a hydrolase activity that specifically cleaves alpha-1,6-glycosidic linkages in oligosaccharides. This enzyme plays a crucial role in carbohydrate metabolism, particularly in the breakdown of complex carbohydrates like glycogen and starch.

The enzyme's active site recognizes and binds to the alpha-1,6-glycosidic linkage. The catalytic mechanism involves the following steps:

1. **Protonation:** A proton from a catalytic residue in the active site is donated to the oxygen atom of the glycosidic bond.
2. **Nucleophilic attack:** A nucleophile, often a water molecule activated by a nearby amino acid residue, attacks the carbon atom at the anomeric position of the glucose residue.
3. **Bond cleavage:** The glycosidic bond breaks, releasing the glucose residue.
4. **Deprotonation:** The proton previously donated to the oxygen atom is removed, regenerating the catalytic residue.

The cleavage of alpha-1,6-glycosidic linkages is essential for several reasons:

* **Glycogen degradation:** In glycogen metabolism, oligo-1,6-glucosidase, also known as debranching enzyme, removes the branch points in glycogen, allowing further breakdown by other enzymes.
* **Starch digestion:** Oligo-1,6-glucosidase contributes to the digestion of starch, which contains alpha-1,6-glycosidic linkages in its branched structure.
* **Regulation of carbohydrate metabolism:** By controlling the breakdown of complex carbohydrates, oligo-1,6-glucosidase indirectly influences blood glucose levels.

Deficiencies in oligo-1,6-glucosidase activity can lead to glycogen storage diseases, characterized by the accumulation of abnormal glycogen in various tissues. This highlights the enzyme's critical role in maintaining normal carbohydrate metabolism.'
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Proteins (1)

ProteinDefinitionTaxonomy
Sucrase-isomaltase, intestinalA sucrase-isomaltase, intestinal that is encoded in the genome of human. [PRO:DNx, UniProtKB:P14410]Homo sapiens (human)

Compounds (30)

CompoundDefinitionClassesRoles
2,4-thiazolidinedione1,3-thiazolidine-2,4-dione : A thiazolidenedione carrying oxo substituents at positions 2 and 4.

thiazolidine-2,4-dione: structure in first source
thiazolidenedione
methyl acetoacetatemethyl acetoacetate: structureoxo carboxylic acid
diethyl malonatediethyl malonate: isomer of diethylmalonic acid; one of most used compounds in drug synthesis, don't confuse with ethylmalonic aciddicarboxylic acid
1-deoxynojirimycin1-deoxy-nojirimycin: structure in first source

duvoglustat : An optically active form of 2-(hydroxymethyl)piperidine-3,4,5-triol having 2R,3R,4R,5S-configuration.
2-(hydroxymethyl)piperidine-3,4,5-triol;
piperidine alkaloid
anti-HIV agent;
anti-obesity agent;
bacterial metabolite;
EC 3.2.1.20 (alpha-glucosidase) inhibitor;
hepatoprotective agent;
hypoglycemic agent;
plant metabolite
acarbosetetrasaccharide derivativeEC 3.2.1.1 (alpha-amylase) inhibitor;
EC 3.2.1.20 (alpha-glucosidase) inhibitor;
geroprotector;
hypoglycemic agent
miglustatmiglustat : A hydroxypiperidine that is deoxynojirimycin in which the amino hydrogen is replaced by a butyl group.

miglustat: a glucosylceramide synthase inhibitor
piperidines;
tertiary amino compound
anti-HIV agent;
EC 2.4.1.80 (ceramide glucosyltransferase) inhibitor
(-)-catechin(-)-catechin : The (-)-enantiomer of catechin.catechinmetabolite
terphenyllinterphenyllin : A para-terphenyl that is 1,1':4',1''-terphenyl substituted by methoxy groups at positions 3' and 6' and hydroxy groups at positions 2', 4 and 4''. It has been isolated from Aspergillus taichungensis.

terphenyllin: novel p-terphenyl metabolite from Aspergillus candidus
dimethoxybenzene;
para-terphenyl;
phenols
Aspergillus metabolite;
mycotoxin
1,4-dideoxy-1,4-iminoarabinitol1,4-dideoxy-1,4-iminoarabinitol: RN given refers to (2S-(2alpha,3beta,4alpha))-isomer; structure given in first source
valiolaminevaliolamine: isolated from Streptomyces hygroscopicus; RN from CA Index; RN not in Chemline 2/85
migalastatmigalastat: a potent inhibitor of glycolipid biosynthesispiperidines
3-hydroxyterphenyllin3-hydroxyterphenyllin : A para-terphenyl that is the 3-hydroxy derivative of terphenyllin. It has been isolated from Aspergillus taichungensis.

3-hydroxyterphenyllin: metabolite of Aspergillus candidus; structure
catechols;
dimethoxybenzene;
para-terphenyl
Aspergillus metabolite
valienaminevalienamine: intermediate formed by microbial degradation of validamycins; structure given in first source
miglitolpiperidines
validaminevalidamine : An amino cyclitol consisting of 1D-chiro-inositol lacking the 6-hydroxy group and having those at positions 1 and 5 replaced by amino and hydroxymethyl groups respectively.

validamine: RN given from CA Index Guide; RN not in Chemline 11/84; structure given in first source
amino cyclitol
2-(Benzotriazol-1-yl)-1-(4-bromophenyl)ethanonearomatic ketoneanticoronaviral agent
trisindolinetrisindoline: an antibiotic indole trimer, produced by Vibrio separated from the marine sponge Hyrtios altum; structure given in first source
quercetin7-hydroxyflavonol;
pentahydroxyflavone
antibacterial agent;
antineoplastic agent;
antioxidant;
Aurora kinase inhibitor;
chelator;
EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor;
geroprotector;
phytoestrogen;
plant metabolite;
protein kinase inhibitor;
radical scavenger
baicaleintrihydroxyflavoneangiogenesis inhibitor;
anti-inflammatory agent;
antibacterial agent;
anticoronaviral agent;
antifungal agent;
antineoplastic agent;
antioxidant;
apoptosis inducer;
EC 1.13.11.31 (arachidonate 12-lipoxygenase) inhibitor;
EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor;
EC 4.1.1.17 (ornithine decarboxylase) inhibitor;
ferroptosis inhibitor;
geroprotector;
hormone antagonist;
plant metabolite;
prostaglandin antagonist;
radical scavenger
mangostinalpha-mangostin : A member of the class of xanthones that is 9H-xanthene substituted by hydroxy group at positions 1, 3 and 6, a methoxy group at position 7, an oxo group at position 9 and prenyl groups at positions 2 and 8. Isolated from the stems of Cratoxylum cochinchinense, it exhibits antioxidant, antimicrobial and antitumour activities.

mangostin: xanthone from rind of Garcinia mangostana Linn. fruit
aromatic ether;
phenols;
xanthones
antimicrobial agent;
antineoplastic agent;
antioxidant;
plant metabolite
7,8-dihydroxy-4-methylcoumarin7,8-dihydroxy-4-methylcoumarin: possess strong antioxidant and radical scavenging activities; structure in first sourcehydroxycoumarin
gamma-mangostingamma-mangostin : A member of the class of xanthones that is 9H-xanthene substituted by hydroxy group at positions 1, 3, 6 and 7, an oxo group at position 9 and prenyl groups at positions 2 and 8. Isolated from the stems of Cratoxylum cochinchinense, it exhibits antitumour activity.phenols;
xanthones
antineoplastic agent;
plant metabolite;
protein kinase inhibitor
beta-Mangostinxanthones
9-Hydroxycalabaxanthonexanthones
n-(5-adamantane-1-yl-methoxy-pentyl)deoxynojirimycin
l-altro-1-deoxynojirimycinL-altro-1-deoxynojirimycin: structure in first source
sch 725680Sch 725680: an aazaphilone from Aspergillus sp.; structure in first source
aspernolide aaspernolide A: structure in first source
aspulvinone E4-hydroxy-5-(4-hydroxybenzylidene)-3-(4-hydroxyphenyl)furan-2(5H)-one : A member of the class of butenolides that is furan-2(5H)-one substituted by 4-hydroxyphenyl, hydroxy and 4-hydroxybenzylidene groups at positions 3, 4 and 5, respectively.

aspulvinone E : A 4-hydroxy-5-(4-hydroxybenzylidene)-3-(4-hydroxyphenyl)furan-2(5H)-one in which the double bond adopts a Z-configuration. It is a marine metabolite isolated from the fungus Aspergillus terreus and exhibits antiviral activity.
4-hydroxy-5-(4-hydroxybenzylidene)-3-(4-hydroxyphenyl)furan-2(5H)-one;
aspulvinone
antiviral agent;
Aspergillus metabolite;
EC 3.2.1.20 (alpha-glucosidase) inhibitor;
marine metabolite
pinophilin bpinophilin B: from cultures of a fungus (Penicillium pinophilum Hedgcok) derived from a seaweed; structure in first source