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3.2.1.114: mannosyl-oligosaccharide 1,3-1,6-alpha-mannosidase

This is an abbreviated version!
For detailed information about mannosyl-oligosaccharide 1,3-1,6-alpha-mannosidase, go to the full flat file.

Word Map on EC 3.2.1.114

Reaction

Man5GlcNAc3-[protein]
+ 2 H2O =
Man3GlcNAc3-[protein]
 + 2 alpha-D-mannopyranose

Synonyms

1,3(1,6)-alpha-D-mannosidase, 1,6-alpha-D-mannosidase, Afams1, alpha-1,3 mannosidase, alpha-1,3-mannosidase, alpha-D-mannosidase II, alpha-mannosidase, alpha-mannosidase II, alpha-mannosidase III, alpha-mannosidase IIx, alpha-MII, alpha1-3,6-mannosidase, Bt3991, class II alpha-D-mannosidase, class II alpha-mannosidase, class IIC alpha-mannosidase, dGMII, Drosophila GMII, exo-1,3-1,6-alpha-mannosidase, GH38 alpha-mannosidase II, GH38 enzyme, GH38 Golgi alpha-mannosidase II, GlcNAc transferase I-dependent alpha1,3[alpha1,6]mannosidase, glycoside hydrolase, GmII, Golgi alpha-mannosidase II, Golgi mannosidase IIx, human type II alpha-mannosidase, jack bean alpha-mannosidase, Man II, MAN IIx, MAN2A1, ManII, ManIII, mannose-trimming enzyme, mannosidase II, mannosidase, exo-1,3-1,6-alpha-, mannosyl-oligosaccharide 1,3-1,6-alpha-mannosidase, mannosyl-oligosaccharide 1,3-1,6-alpha-mannosidase II, MII, More, NAM, neutral alpha-mannosidase, SpGH38, TM1851

ECTree

     3 Hydrolases
         3.2 Glycosylases
             3.2.1 Glycosidases, i.e. enzymes that hydrolyse O- and S-glycosyl compounds
                3.2.1.114 mannosyl-oligosaccharide 1,3-1,6-alpha-mannosidase

Inhibitors

Inhibitors on EC 3.2.1.114 - mannosyl-oligosaccharide 1,3-1,6-alpha-mannosidase

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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(1R,2R,3R,4R,5S)-1-(methylthio)-2,3,4-trihydroxy-5-(N-(p-allyl-ester-benzyl)amino)cyclopentane
-
-
(1R,2R,3R,4R,5S)-1-(methylthio)-2,3,4-trihydroxy-5-(N-(p-bromo-benzyl)amino)cyclopentane
-
-
(1R,2R,3R,4R,5S)-1-(methylthio)-2,3,4-trihydroxy-5-(N-(p-chloro-benzyl)amino)cyclopentane
-
-
(1R,2R,3R,4R,5S)-1-(methylthio)-2,3,4-trihydroxy-5-(N-(p-fluoro-benzyl)amino)cyclopentane
-
-
(1R,2R,3R,4R,5S)-1-(methylthio)-2,3,4-trihydroxy-5-(N-(p-methoxy-benzyl)amino)cyclopentane
-
-
(1R,2R,3R,4R,5S)-1-(methylthio)-2,3,4-trihydroxy-5-(N-benzylamino)cyclopentane
-
-
(1R,2R,3R,4S,5R)-4-amino-5-methoxycyclopentane-1,2,3-triol
-
(1R,2R,3R,4S,5S)-1,2,3,4-tetrahydroxy-5-(N-(p-allyl ester benzyl)amino)cyclopentane
-
-
(1R,2R,3R,4S,5S)-1,2,3,4-tetrahydroxy-5-(N-(p-bromo-benzyl)amino)cyclopentane
-
-
(1R,2R,3R,4S,5S)-1,2,3,4-tetrahydroxy-5-(N-(p-chloro-benzyl)amino)cyclopentane
-
-
(1R,2R,3R,4S,5S)-1,2,3,4-tetrahydroxy-5-(N-(p-fluoro-benzyl)amino)cyclopentane
-
-
(1R,2R,3R,4S,5S)-1,2,3,4-tetrahydroxy-5-(N-(p-methoxy-benzyl)amino)cyclopentane
-
-
(1R,2R,3R,4S,5S)-1,2,3,4-tetrahydroxy-5-(N-benzylamino)cyclopentane
-
-
(1R,2R,3S,4R,5R)-5-aminocyclopentane-1,2,3,4-tetrol
-
(1R,2S,3R,4R,5R)-5-aminocyclopentane-1,2,3,4-tetraol
-
(1R,2S,8aS)-1,2-dihydroxyoctahydrothieno[1,2-a]thiopyranium chloride
good inhibitor, lacks a hydroxyl group at C-5, more than 140fold better inhibitor of GMII than di-epi-swainsonine
(1R,6R,7R,8S)-7,8-dihydroxy-5-thia-1-thioniabicyclo[4.3.0]nonane chloride
-
synthetic inhibitor, selective and potent inhibition at 1 mM, 97% inhibition of the activity of the liver lysosomal fraction at pH 4.0, 100% at pH 6.5
(1S,2R,5R,8R,8aR)-5-[2-(4-tert-butylphenyl)ethyl]octahydroindolizine-1,2,8-triol
-
(1S,2R,5S,8R,8aR)-5-[2-(4-tert-butylphenyl)ethyl]octahydroindolizine-1,2,8-triol
-
(1S,2R,6R,7R,8S,8aS)-octahydroindolizine-1,2,6,7,8-pentol
most active
(1S,2R,8R,8aR)-octahydroindolizine-1,2,8-triol
-
(2R,3R,4R,5R)-2-(hydroxymethyl)piperidine-3,4,5-triol
-
(2R,3R,4R,5R)-5-amino-2-(hydroxymethyl)piperidine-3,4-diol
-
(2R,3R,4S)-2-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)pyrrolidine-3,4-diol
(2R,3R,4S)-2-([[(1S)-2-hydroxy-1-phenylethyl]amino]methyl)pyrrolidine-3,4-diol
-
(2R,3R,4S)-2-[[((1R)-2-hydroxy-1-[4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl]ethyl)amino] methyl]pyrrolidine-3,4-diol
-
inhibits the proliferation of primary cells and cell lines of different origins, irrespective of Bcl-2 expression levels, inducing a G2/Mcell cycle arrest and by modification of genes involved in cell cycle progression and survival, IC50 in vivo and cytotoxic effects in different cell lines, overview
(2R,3R,4S)-2[([(1R)-2-hydroxy-1-(4-methoxyphenyl)ethyl]amino)-methyl]pyrrolidine-3,4-diol
-
-
(2R,3R,4S)-2[[((1R)-1-[1,1'-biphenyl]-4-yl-2-hydroxyethyl)amino]-methyl]pyrrolidine-3,4-diol
-
-
(2R,3R,4S)-2[[((1R)-2-hydroxy-1-(4-(phenylmethoxy)phenyl)ethyl)amino]methyl]pyrrolidine-3,4-diol
-
-
(2R,3R,4S)-2[[((1R)-2-hydroxy-1-[4-(2-thienyl)phenyl]ethyl)-amino]methyl]pyrrolidine-3,4-diol
-
-
(2R,3R,4S)-2[[((1R)-2-hydroxy-1-[4-(prop-2-enyloxy)phenyl]-ethyl)amino]methyl] pyrrolidine-3,4-diol
-
-
(2R,3R,4S,5R)-2-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)-5-methylpyrrolidine-3,4-diol
-
(2R,3R,4S,5S)-6-amino-2-(hydroxymethyl)-2,3,4,5-tetrahydropyridine-3,4,5-triol
-
(2R,3S,4R)-2-[(1R)-1-hydroxyethyl]pyrrolidine-3,4-diol
most active
(2R,3S,4S)-1-[(2S,3S)-2,4-dihydroxy-3-(sulfooxy)butyl]-3,4-dihydroxy-2-(hydroxymethyl)tetrahydrothiophenium
-
(2S,3R,4S)-2-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)pyrrolidine-3,4-diol
(2S,3R,4S)-2-[([(1R)-2-[(4-bromophenyl)(hydroxy)methoxy]-1-phenylethyl]amino)methyl]pyrrolidine-3,4-diol
-
-
(3R,4R)-4-aminopyrrolidin-3-ol
-
(3R,4R,5R)-3,4-dihydroxy-5-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)-1-methylpyrrolidin-2-one
-
(3R,4R,5R)-3,4-dihydroxy-5-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)pyrrolidin-2-one
-
(3R,4R,5S)-3,4-dihydroxy-5-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)-1-methylpyrrolidin-2-one
(3R,4R,5S)-3,4-dihydroxy-5-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)pyrrolidin-2-one
(3R,4R,5S)-5-[([(1R)-2-[(4-bromophenyl)(hydroxy)methoxy]-1-phenylethyl]amino)methyl]-3,4-dihydroxy-1-methylpyrrolidin-2-one
-
-
(3R,4R,5S)-5-[([(1R)-2-[(4-bromophenyl)(hydroxy)methoxy]-1-phenylethyl]amino)methyl]-3,4-dihydroxypyrrolidin-2-one
-
-
(3S,4S,5R,6R,E)-3,4,5-trihydroxy-6-(hydroxymethyl)piperidin-2-one O-4-chlorophenylcarbamoyl oxime
-
(5R,6R,7S,8R)-5-methyl-1,5,6,7,8,8a-hexahydrotetrazolo[1,5-a]pyridine-6,7,8-triol
-
(5R,6R,7S,8S)-5-(hydroxymethyl)-1,5,6,7,8,8a-hexahydroimidazo[1,2-a]pyridine-6,7,8-triol
-
(RS)-2-phenylethyl alpha-D-mannopyranosyl sulfoxide
-
-
1,4-Dideoxy-1,4-imino-D-mannitol
1-(4-methylphenyl)-2-[(1S,2R,5R,8R,8aR)-1,2,8-trihydroxyoctahydroindolizin-5-yl]ethanone
-
1-(4-tert-butylphenyl)-2-[(1S,2R,5R,8R,8aR)-1,2,8-trihydroxyoctahydroindolizin-5-yl]ethanone
-
1-(4-tert-butylphenyl)-2-[(1S,2R,5S,8R,8aR)-1,2,8-trihydroxyoctahydroindolizin-5-yl]ethanone
-
1-deoxyamino-cyclopentitetrol
-
-
1-deoxyaminocyclopentitetrol
1-deoxymannojirimycin
1-phenyl-2-[(1S,2R,5R,8R,8aR)-1,2,8-trihydroxyoctahydroindolizin-5-yl]ethanone
-
2-deoxy-2-fluoro-alpha-D-mannosyl fluoride
reversible, D341N mutant GMII
2-O-alpha-D-mannopyranosyl-alpha-D-mannopyranoside
-
in decreasing order of efficiency: alpha1,2, alpha 1,3 and alpha1,6-mannosylmannose
2-phenylethyl alpha-D-mannopyranosyl sulfone
-
-
3-O-alpha-D-mannopyranosyl-alpha-D-mannopyranoside
-
in decreasing order of efficiency: alpha1,2, alpha 1,3 and alpha1,6-mannosylmannose
5-fluoro-beta-L-gulosyl fluoride
reversible, wild-type and D341N mutant GMII, inhibits only at low assay temperatures, acts as slow substrate at 37°C
5-thio-alpha-D-mannopyranosylamine
-
6-O-alpha-D-mannopyranosyl-alpha-D-mannopyranoside
-
in decreasing order of efficiency: alpha1,2, alpha 1,3 and alpha1,6-mannosylmannose
8,8a-di-epi-swainsonine
-
-
8-epi-lentiginosine
-
8a-epi-swainsonine
-
-
alpha-1,6-linked trisaccharide of mannose
-
1.5 mM, 40% inhibition
BAPTA
-
i.e. 1,2-bis(2-aminophenoxy) ethane N,N,N',N'-tetraacetic acid
benzyl alpha-D-mannopyranosyl sulfone
-
-
D-mannonolactam amidrazone
deoxymannojirimycin
di-epi-swainsonine
weak inhibitor
diastereomer of salacinol
-
diastereomer of seleno-salacinol
-
EGTA
-
ethylene glycol-bis(beta-aminoethylether)-N,N,N',N'-tetraacetic acid
Fe3+
-
less potent inhibitor than Fe2+ and Cu2+, 1 mM, 24-30% inhibition
gluco-hydroxyiminolactam
-
guanidinium hydrochloride
-
the enzyme loses 54% and 70% of the original activity in 0.5 M and 1.0 M guanidinium hydrochloride, respectively. Irreversible denaturation at higher concentration of 6 M of guanidinium hydrochloride, kinetics, overview. The protein almost completely unfolds in 4.0 M guanidinium hydrochloride
kifunensine
mannose
-
250 mM, 30% inhibition
mannostatin
Mannostatin A
mannostatin B
strong inhibitor, reversible, competitive
Mannosyl-mannose disaccharide
-
in decreasing order of efficiency: alpha1,2, alpha 1,3 and alpha1,6-mannosylmannose
-
meso-aminocyclopentitretrol
-
-
N-benzyl mannostatin A
-
structural basis of the inhibition of Golgi alpha-mannosidase II and the role of the thiomethyl moiety in ligand-protein interactions, overview
N-benzyl-mannostatin
-
-
N-octyl-6-epi-valienamine
-
N-[(R)-amino(phenyl)methyl]-5-thio-alpha-D-mannopyranosylamine
-
noeuromycin
p-chloromercuriphenylsulfonate
PCMB
-
Ca2+ protects
phosphatidylinositol
-
CaCl2 or NaCl restores
swainsonine
[[(3S,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)piperidin-2-ylidene]amino] N-(4-chlorophenyl)carbamate
-
additional information
-