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- Name help_outline β-D-gentiobiosyl crocetin Identifier CHEBI:62770 Charge -1 Formula C32H43O14 InChIKeyhelp_outline VULLCGFNYWDRHL-YJOFKXFJSA-M SMILEShelp_outline CC(\C=C\C=C(/C)C([O-])=O)=C/C=C/C=C(C)/C=C/C=C(\C)C(=O)O[C@@H]1O[C@H](CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 2 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 InChIKeyhelp_outline HSCJRCZFDFQWRP-JZMIEXBBSA-L SMILEShelp_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 β-D-gentiobiosyl β-D-glucosyl crocetin Identifier CHEBI:62771 Charge 0 Formula C38H54O19 InChIKeyhelp_outline CZSBHMFVVLYIQQ-DRVLGOCHSA-N SMILEShelp_outline CC(\C=C\C=C(/C)C(=O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)=C/C=C/C=C(C)/C=C/C=C(\C)C(=O)O[C@@H]1O[C@H](CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 3 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 InChIKeyhelp_outline XCCTYIAWTASOJW-XVFCMESISA-K SMILEShelp_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 577 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
RHEA:31471 | RHEA:31472 | RHEA:31473 | RHEA:31474 | |
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Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Publications
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Glucosylation of the saffron apocarotenoid crocetin by a glucosyltransferase isolated from Crocus sativus stigmas.
Moraga A.R., Nohales P.F., Perez J.A., Gomez-Gomez L.
Saffron, the dry stigma of Crocus sativus L., is considered to be the world's most expensive spice. Three major apocarotenoids--crocin, crocetin and picrocrocin--are responsible for the colour and bitter taste of saffron. The final step in the biosynthesis of the 20-carbon esterified carotenoid cr ... >> More
Saffron, the dry stigma of Crocus sativus L., is considered to be the world's most expensive spice. Three major apocarotenoids--crocin, crocetin and picrocrocin--are responsible for the colour and bitter taste of saffron. The final step in the biosynthesis of the 20-carbon esterified carotenoid crocin is the transformation of the insoluble crocetin into a soluble and stable storage form by glucosylation. These glucosylation reactions are catalysed by glucosyltransferases (GTases) that play a crucial role in natural-product biosynthesis. Using degenerate primers designed to match the plant secondary product GTase (PSPG) box we cloned two cDNAs, UGTCs2 and UGTCs3, from C. sativus stigmas that encode putative polypeptides of 460 and 475 amino acids, respectively. These genes were expressed differentially in saffron tissues. UGTCs2 was mainly expressed in fully developed stigmas, whereas UGTCs3 was mainly expressed in stamens. The UGTCs2 transcript was not detected in the stigma tissue of a Crocus species that does not synthesize crocin, while UGTCs3 and other structural genes for carotenoid biosynthesis were expressed in the stigma of all tested Crocus species. To identify the biochemical function of UGTCs2, the isolated cDNA was expressed in Escherichia coli cells. The recombinant protein UGTCs2 had glucosylation activity against crocetin, crocetin beta-D-glucosyl ester and crocetin beta-D-gentibiosyl ester. These results might suggest that the isolated clone UGTCs2 codes for a saffron crocetin GTase. << Less
Planta 219:955-966(2004) [PubMed] [EuropePMC]
This publication is cited by 2 other entries.
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UGT75L6 and UGT94E5 mediate sequential glucosylation of crocetin to crocin in Gardenia jasminoides.
Nagatoshi M., Terasaka K., Owaki M., Sota M., Inukai T., Nagatsu A., Mizukami H.
Crocin is an apocarotenoid glycosyl ester accumulating in fruits of Gardenia jasminoides and used as a food coloring and nutraceutical. For the first time, the two glucosyltransferases UGT75L6 and UGT94E5 that sequentially mediate the final glucosylation steps in crocin biosynthesis in G. jasminoi ... >> More
Crocin is an apocarotenoid glycosyl ester accumulating in fruits of Gardenia jasminoides and used as a food coloring and nutraceutical. For the first time, the two glucosyltransferases UGT75L6 and UGT94E5 that sequentially mediate the final glucosylation steps in crocin biosynthesis in G. jasminoides have been identified and functionally characterized. UGT75L6 preferentially glucosylates the carboxyl group of crocetin yielding crocetin glucosyl esters, while UGT94E5 glucosylates the 6' hydroxyl group of the glucose moiety of crocetin glucosyl esters. The expression pattern of neither UGT75L6 nor UGT94E5 correlated with the pattern of crocin accumulation in G. jasminoides. << Less
FEBS Lett. 586:1055-1061(2012) [PubMed] [EuropePMC]
This publication is cited by 5 other entries.