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Information on EC 2.4.1.178 - hydroxymandelonitrile glucosyltransferase

for references in articles please use BRENDA:EC2.4.1.178

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EC Tree

2 Transferases

2.4 Glycosyltransferases

2.4.1 Hexosyltransferases

2.4.1.178 hydroxymandelonitrile glucosyltransferase

IUBMB Comments

3,4-Dihydroxymandelonitrile can also act as acceptor.

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The enzyme appears in viruses and cellular organisms

Reaction Schemes

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UDP-glucose

4-hydroxymandelonitrile

UDP

taxiphyllin

Synonyms

cyanohydrin glucosyltransferase, glucosyltransferase, uridine diphosphoglucose-cyanohydrin, UDPglucose:4-hydroxymandelonitrile glucosyltransferase, show all synonyms

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SYNONYM

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

cyanohydrin glucosyltransferase

glucosyltransferase, uridine diphosphoglucose-cyanohydrin

UDPglucose:4-hydroxymandelonitrile glucosyltransferase

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REACTION

REACTION DIAGRAM

COMMENTARY

ORGANISM

UNIPROT

LITERATURE

UDP-glucose + 4-hydroxymandelonitrile = UDP + taxiphyllin

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REACTION TYPE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

hexosyl group transfer

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PATHWAY SOURCE

PATHWAYS

MetaCyc

3,4-dihydroxymandelonitrile beta-D-glucose biosynthesis, taxiphyllin biosynthesis

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SYSTEMATIC NAME

IUBMB Comments

UDP-glucose:4-hydroxymandelonitrile glucosyltransferase

3,4-Dihydroxymandelonitrile can also act as acceptor.

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CAS REGISTRY NUMBER

COMMENTARY

89287-39-8

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SUBSTRATE

PRODUCT

REACTION DIAGRAM

ORGANISM

UNIPROT

COMMENTARY
(Substrate)

LITERATURE
(Substrate)

COMMENTARY
(Product)

LITERATURE
(Product)

Reversibility
r=reversible
ir=irreversible
?=not specified

UDP-glucose + (R,S)-mandelonitrile

UDP + (R)-prunasin

Prunus serotina

639554

UDP-glucose + 3,4-dihydroxymandelonitrile

UDP + 3,4-dihydroxymandelonitrile glucoside

Triglochin maritima

587060

UDP-glucose + 4-hydroxymandelonitrile

UDP + taxiphyllin

2 entries

UDP-glucose + benzoic acid

UDP + benzoyl-beta-D-glucoside

Prunus serotina

639554

UDP-glucose + benzyl alcohol

UDP + benzyl-beta-D-glucoside

Prunus serotina

639554

UDP-glucose + mandelamide

Prunus serotina

639554

UDP-glucose + mandelic acid

Prunus serotina

639554

UDP-glucose + 4-hydroxymandelonitrile

UDP + taxiphyllin

Triglochin maritima

587060

UDP-glucose + 4-hydroxymandelonitrile

UDP + taxiphyllin

Triglochin maritima

last step in biosynthesis of cyanogenic glucosides

587060

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NATURAL SUBSTRATE

NATURAL PRODUCT

REACTION DIAGRAM

ORGANISM

UNIPROT

COMMENTARY
(Substrate)

LITERATURE
(Substrate)

COMMENTARY
(Product)

LITERATURE
(Product)

REVERSIBILITY
r=reversible
ir=irreversible
?=not specified

UDP-glucose + (R,S)-mandelonitrile

UDP + (R)-prunasin

Prunus serotina

639554

UDP-glucose + 4-hydroxymandelonitrile

UDP + taxiphyllin

Triglochin maritima

last step in biosynthesis of cyanogenic glucosides

587060

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METALS and IONS

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

High salt concentrations

Triglochin maritima

160% activity observed at 0.6 M concentration of NaCl, KCl or ammonium sulfate with 4-hydroxymandelonitrile, and 20% activity observed at 0.1-0.2 M concentration with 3,4-dihydroxymandelonitrile

587060

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KM VALUE [mM]

SUBSTRATE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

0.32 - 0.5

UDP-glucose

2 entries

0.32

UDP-glucose

Prunus serotina

assay at pH 7.3 in the presence of 20 mM of (R,S)-mandelonitrile. The enzyme exclusively utilizes the (R)-enantiomer

639554

0.5

UDP-glucose

Triglochin maritima

4-hydroxymandelonitrile or 3,4-dihydroxymandelonitrile

587060

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SPECIFIC ACTIVITY [µmol/min/mg]

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

0.001

mandelic acid

0.002

benzyl alcohol

0.0025

mandelamide

0.012

S)-mandelonitrile

0.018

benzoic acid

0.31

3,4-dihydroxymandelonitrile

587060

0.94

Triglochin maritima

4-hydroxymandelonitrile

587060

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pH OPTIMUM

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

6.5 - 8.5

Triglochin maritima

587060

7 - 8

Prunus serotina

highest rates are realized in Tris-HCl buffer at pH 7.5

assay at

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pH RANGE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

5.8 - 9.3

Prunus serotina

about 50% of activity maximum

639554

6 - 9.5

Triglochin maritima

about 50% of activity maximum at pH 6 and pH 9.5

587060

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TEMPERATURE OPTIMUM

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

Triglochin maritima

587060

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ORGANISM

COMMENTARY

LITERATURE

UNIPROT

SEQUENCE DB

SOURCE

wild black cherry

brenda

brenda

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SOURCE TISSUE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

SOURCE

brenda

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LOCALIZATION

ORGANISM

UNIPROT

COMMENTARY

GeneOntology No.

LITERATURE

SOURCE

brenda

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MOLECULAR WEIGHT

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

47000

1 * 47000, SDS-PAGE

50000

gel filtration

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SUBUNIT

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

monomer

Triglochin maritima

1 * 47000, SDS-PAGE

587060

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pH STABILITY

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

7.5

Triglochin maritima

unstable below, crude enzyme extract

587060

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STORAGE STABILITY

ORGANISM

UNIPROT

LITERATURE

-20°C, 10% glycerol, 72% of 2 days crude extract stable for several weeks

Prunus serotina

639554

-20°C, 10% glycerol, crude extract stable for several weeks

Triglochin maritima

587060

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PURIFICATION (Commentary)

ORGANISM

UNIPROT

LITERATURE

method that includes chromatography on Sephadex G-25

Prunus serotina

639554

method that includes chromatography on Sephadex PD10 and DEAE-Sephadex

Triglochin maritima

587060

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REF.

AUTHORS

TITLE

JOURNAL

VOL.

PAGES

YEAR

ORGANISM (UNIPROT)

PUBMED ID

SOURCE

587060

Hösel, W.; Schiel, O.

Biosynthesis of cyanogenic glucosides: in vitro analysis of the glucosylation step

Arch. Biochem. Biophys.

229

177-186

1984

Triglochin maritima

6230992

brenda

639554

Poulton, J.E.; Shin, S.I.

Prunasin biosynthesis by cell-free extracts from black cherry (Prunus serotina Ehrh.) fruits and leaves

Z. Naturforsch. C

369-374

1983

Prunus serotina

brenda

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EXTERNAL LINKS (specific for EC-Number 2.4.1.178)

NCBI: PubMed, Protein, Nucleotide, Structure, Gene, OMIM

IUBMB Enzyme Nomenclature

UniProt

PDB

PROSITE Database of protein families and domains

InterPro (database of protein families, domains and functional sites)

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