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2.3.1.106

Accepted name:

tartronate O-hydroxycinnamoyltransferase

Reaction:

sinapoyl-CoA + 2-hydroxymalonate = CoA + sinapoyltartronate

For diagram of reaction, click here

Glossary:

sinapate = 4-hydroxy-3,5-dimethoxycinnamate
tartronate = 2-hydroxymalonate

Other name(s):

tartronate sinapoyltransferase; hydroxycinnamoyl-coenzyme-A:tartronate hydroxycinnamoyltransferase

Systematic name:

sinapoyl-CoA:2-hydroxymalonate O-(hydroxycinnamoyl)transferase

Comments:

4-Coumaroyl-CoA (4-hydroxycinnamoyl-CoA), caffeoyl-CoA (3,4-dihydroxycinnamoyl-CoA) and feruloyl-CoA (4-hydroxy-3-methoxycinnamoyl-CoA) can also act as donors for the enzyme from the mung bean (Vigna radiata).

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number: 102484-57-1

References:

1.	Strack, D., Ruhoff, R. and Gräwe, W. Hydroxycinnamoyl-Coenzyme-A-tartronate hydroxycinnamoyltransferase in protein preparations from mung bean. Phytochemistry 25 (1986) 833–837.

[EC 2.3.1.106 created 1989, modified 1990, modified 2002]

2.4.1.120

Accepted name:

sinapate 1-glucosyltransferase

Reaction:

UDP-α-D-glucose + sinapate = UDP + 1-O-sinapoyl-β-D-glucose

Glossary:

sinapate = (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate

Other name(s):

uridine diphosphoglucose-sinapate glucosyltransferase; UDP-glucose:sinapic acid glucosyltransferase; uridine 5′-diphosphoglucose-hydroxycinnamic acid acylglucosyltransferase; UDP-glucose:sinapate D-glucosyltransferase

Systematic name:

UDP-α-D-glucose:sinapate D-glucosyltransferase

Comments:

Some other hydroxycinnamates, including 4-coumarate, ferulate and caffeate, can act as acceptors, but more slowly. Only glucose esters, not glucosides, are formed (cf. EC 2.4.1.126 hydroxycinnamate 4-β-glucosyltransferase).

Links to other databases:

BRENDA, EXPASY, GTD, KEGG, MetaCyc, CAS registry number: 74082-53-4

References:

1.	Strack, D. Enzymatic synthesis of 1-sinapoylglucose from free sinapic acid and UDP-glucose by a cell free system from Raphanus sativus seedlings. Z. Naturforsch. C: Biosci. 35 (1980) 204–208.

[EC 2.4.1.120 created 1984]

2.4.1.126

Accepted name:

hydroxycinnamate 4-β-glucosyltransferase

Reaction:

UDP-glucose + trans-4-hydroxycinnamate = UDP + 4-O-β-D-glucosyl-4-hydroxycinnamate

Other name(s):

uridine diphosphoglucose-hydroxycinnamate glucosyltransferase; UDP-glucose-hydroxycinnamate glucosyltransferase; hydroxycinnamoyl glucosyltransferase

Systematic name:

UDP-glucose:trans-4-hydroxycinnamate 4-O-β-D-glucosyltransferase

Comments:

Acts on 4-coumarate, ferulate, caffeate and sinapate, forming a mixture of 4-glucosides and glucose esters (cf. EC 2.4.1.120 sinapate 1-glucosyltransferase).

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number: 77848-85-2

References:

1.	Fleuriet, A., Macheix, J.J., Suen, R. and Ibrahim, R.K. Partial purifiction and some properties of a hydroxycinnamoyl glucosyltransferase from tomato fruits. Z. Naturforsch. C: Biosci. 35 (1980) 967–972.

[EC 2.4.1.126 created 1984]

2.4.1.299

Accepted name:

cyanidin 3-O-glucoside 5-O-glucosyltransferase (acyl-glucose)

Reaction:

1-O-sinapoyl-β-D-glucose + cyanidin 3-O-β-D-glucoside = sinapate + cyanidin 3,5-di-O-β-D-glucoside

For diagram of anthocyanidin glucoside biosynthesis, click here

Glossary:

sinapate = 4-hydroxy-3,5-dimethoxycinnamate
cyanidin = 3,3′,4′,5,7-pentahydroxyflavylium

Other name(s):

AA5GT

Systematic name:

1-O-sinapoyl-β-D-glucose:cyanidin-3-O-β-D-glucoside 5-O-β-D-glucosyltransferase

Comments:

Isolated from the plant Dianthus caryophyllus (carnation). Also acts on other anthocyanidins and with other acyl-glucose donors. cf. EC 2.4.1.298, anthocyanidin 3-O-glucoside 5-O-glucosyltransferase.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc

References:

1.	Matsuba, Y., Sasaki, N., Tera, M., Okamura, M., Abe, Y., Okamoto, E., Nakamura, H., Funabashi, H., Takatsu, M., Saito, M., Matsuoka, H., Nagasawa, K. and Ozeki, Y. A novel glucosylation reaction on anthocyanins catalyzed by acyl-glucose-dependent glucosyltransferase in the petals of carnation and delphinium. Plant Cell 22 (2010) 3374–3389. [DOI] [PMID: 20971893]
2.	Nishizaki, Y., Matsuba, Y., Okamoto, E., Okamura, M., Ozeki, Y. and Sasaki, N. Structure of the acyl-glucose-dependent anthocyanin 5-O-glucosyltransferase gene in carnations and its disruption by transposable elements in some varieties. Mol. Genet. Genomics 286 (2011) 383–394. [DOI] [PMID: 22048706]

[EC 2.4.1.299 created 2013]

3.1.1.49

Accepted name:

sinapine esterase

Reaction:

sinapoylcholine + H₂O = sinapate + choline

Other name(s):

aromatic choline esterase

Systematic name:

sinapoylcholine sinapohydrolase

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number: 72506-67-3

References:

1.	Nurmann, G. and Strack, D. Sinapine esterase. 1. Characterization of sinapine esterase from cotyledons of Raphanus sativus. Z. Naturforsch. C: Biosci. 34 (1979) 715–720.

[EC 3.1.1.49 created 1984]

4.1.2.66

Accepted name:

4-coumarate hydratase/lyase

Reaction:

4-coumarate + H₂O = 4-hydroxybenzaldehyde + acetate (overall reaction)
(1a) 4-coumarate + H₂O = 3-hydroxy-3-(4-hydroxyphenyl)propanoate
(1b) 3-hydroxy-3-(4-hydroxyphenyl)propanoate = 4-hydroxybenzaldehyde + acetate

Glossary:

4-coumarate = (2E)-3-(4-hydroxyphenyl)acrylate = (2E)-3-(4-hydroxyphenyl)prop-2-enoate

Other name(s):

4-hydroxybenzaldehyde synthase; 4HBS

Systematic name:

4-coumarate acetate-lyase (4-hydroxybenzaldehyde-forming)

Comments:

The enzyme has been purified from vanilla pods of the orchid Vanilla planifolia. It is highly specific for 4-coumarate. Similar compounds such as cinnamate, caffeate, sinapate and o-coumarate are not substrates.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc

References:

1.	Podstolski, A., Havkin-Frenkel, D., Malinowski, J., Blount, J.W., Kourteva, G. and Dixon, R.A. Unusual 4-hydroxybenzaldehyde synthase activity from tissue cultures of the vanilla orchid Vanilla planifolia. Phytochemistry 61 (2002) 611–620. [DOI] [PMID: 12423881]

[EC 4.1.2.66 created 2024]