Rhea - reaction knowledgebase

Enzymes

UniProtKB ^help_outline	1 proteins
Enzyme class ^help_outline	EC 2.4.1.192 nuatigenin 3beta-glucosyltransferase
GO Molecular Function ^help_outline	GO:0047248 nuatigenin 3-beta-glucosyltransferase activity

Reaction participants Show >> << Hide

Name ^help_outline nuatigenin Identifier CHEBI:15574 (CAS: 6811-35-4) ^help_outline Charge 0 Formula C27H42O4 InChIKey^help_outline NELZMZLNTYWIPD-MLBSDYKWSA-N SMILES^help_outline [H][C@]12C[C@@]3([H])[C@]4([H])CC=C5C[C@@H](O)CC[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]1([H])[C@H](C)[C@@]1(CC[C@@](C)(CO)O1)O2 2D coordinates Mol file for the small molecule Search links Involved in 1 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name ^help_outline UDP-α-D-glucose Identifier CHEBI:58885 (Beilstein: 3827329) ^help_outline Charge -2 Formula C15H22N2O17P2 InChIKey^help_outline HSCJRCZFDFQWRP-JZMIEXBBSA-L SMILES^help_outline OC[C@H]1O[C@H](OP([O-])(=O)OP([O-])(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)n2ccc(=O)[nH]c2=O)[C@H](O)[C@@H](O)[C@@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 231 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name ^help_outline H⁺ Identifier CHEBI:15378 Charge 1 Formula H InChIKey^help_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILES^help_outline [H+] 2D coordinates Mol file for the small molecule Search links Involved in 9,431 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name ^help_outline nuatigenin 3-β-D-glucopyranoside Identifier CHEBI:15575 Charge 0 Formula C33H52O9 InChIKey^help_outline QJEQHVALLZCTGC-HPNIRRCESA-N SMILES^help_outline [H][C@]12C[C@@]3([H])[C@]4([H])CC=C5C[C@H](CC[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]1([H])[C@H](C)[C@@]1(CC[C@@](C)(CO)O1)O2)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 1 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name ^help_outline UDP Identifier CHEBI:58223 Charge -3 Formula C9H11N2O12P2 InChIKey^help_outline XCCTYIAWTASOJW-XVFCMESISA-K SMILES^help_outline O[C@@H]1[C@@H](COP([O-])(=O)OP([O-])([O-])=O)O[C@H]([C@@H]1O)n1ccc(=O)[nH]c1=O 2D coordinates Mol file for the small molecule Search links Involved in 576 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule

Cross-references

	RHEA:19329	RHEA:19330	RHEA:19331	RHEA:19332
Reaction direction	undefined	left-to-right	right-to-left	bidirectional
UniProtKB ^help_outline	1 proteins	1 proteins
EC numbers ^help_outline	2.4.1.192
Gene Ontology ^help_outline	GO:0047248
KEGG ^help_outline				R04577
MetaCyc ^help_outline		2.4.1.192-RXN

Related reactions ^help_outline

More general form(s) of this reaction

RHEA:22724
a sterol + UDP-α-D-glucose = a sterol 3-β-D-glucoside + H⁺ + UDP

Publications

A novel glucosyltransferase involved in steroid saponin biosynthesis in Solanum aculeatissimum.

Kohara A., Nakajima C., Hashimoto K., Ikenaga T., Tanaka H., Shoyama Y., Yoshida S., Muranaka T.

Steroidal saponins are widely distributed in many plant species. Their diverse structures have resulted in a wide range of applications, including drug and medicine production. It has been suggested that the nature of the non-saccharide and oligosaccharide portions of the saponin molecule both con ... >> More

Steroidal saponins are widely distributed in many plant species. Their diverse structures have resulted in a wide range of applications, including drug and medicine production. It has been suggested that the nature of the non-saccharide and oligosaccharide portions of the saponin molecule both contribute to the properties of individual saponins. Despite numerous studies on the occurrence, chemical structure, and varying pharmaceutical activities of steroidal saponins, their biosynthesis pathway is poorly understood. Glycosylation is thought to be the final step in steroidal saponin biosynthesis and it is thought to be involved in regulating the biological activities of saponins. Isolation of the glycosyltransferases that catalyze the transfer of sugar molecules to steroidal compounds will help to clarify the mechanisms that produce diverse saponins and control their activities in plants. In this study, we obtained three cDNAs encoding putative glycosyltransferases from Solanum aculeatissimum. One of the three, SaGT4A showed UDP-glucosyltransferase activity. This is the first cloned glucosyltransferase involved in steroidal saponin biosynthesis. SaGT4A catalyzes the 3-O-glucosylation of steroidal sapogenins, such as diosgenin, nuatigenin, and tigogenin. This enzyme also glucosylates steroidal alkaloids, such as solanidine, solasodine, and tomatidine. Gene expression analysis revealed that the accumulation of SaGT4A transcripts showed a unique response to wounding stress indicating the involvement of SaGT4A in plant defense system. << Less

Plant Mol. Biol. 57:225-239(2005) [PubMed] [EuropePMC]

This publication is cited by 4 other entries.

Comments

Published in: Kalinowska, M. and Wojciechowski, Z.A. Enzymatic-synthesis of nuatigenin 3-beta-D-glucoside in oat (Avena sativa) leaves. Phytochemistry 25 (1986) 2525–2529. Kalinowska, M. and Wojciechowski, Z.A. Subcellular-localization of UDPG-nuatigenin glucosyltransferase in oat leaves. Phytochemistry 26 (1987) 353–357.