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- Name help_outline butan-1-ol Identifier CHEBI:28885 (CAS: 71-36-3) help_outline Charge 0 Formula C4H10O InChIKeyhelp_outline LRHPLDYGYMQRHN-UHFFFAOYSA-N SMILEShelp_outline CCCCO 2D coordinates Mol file for the small molecule Search links Involved in 12 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline butanoyl-CoA Identifier CHEBI:57371 Charge -4 Formula C25H38N7O17P3S InChIKeyhelp_outline CRFNGMNYKDXRTN-CITAKDKDSA-J SMILEShelp_outline CCCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP([O-])(=O)OP([O-])(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP([O-])([O-])=O)n1cnc2c(N)ncnc12 2D coordinates Mol file for the small molecule Search links Involved in 37 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline butyl butanoate Identifier CHEBI:87429 (CAS: 109-21-7) help_outline Charge 0 Formula C8H16O2 InChIKeyhelp_outline XUPYJHCZDLZNFP-UHFFFAOYSA-N SMILEShelp_outline CCCCOC(=O)CCC 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 CoA Identifier CHEBI:57287 (Beilstein: 11604429) help_outline Charge -4 Formula C21H32N7O16P3S InChIKeyhelp_outline RGJOEKWQDUBAIZ-IBOSZNHHSA-J SMILEShelp_outline CC(C)(COP([O-])(=O)OP([O-])(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP([O-])([O-])=O)n1cnc2c(N)ncnc12)[C@@H](O)C(=O)NCCC(=O)NCCS 2D coordinates Mol file for the small molecule Search links Involved in 1,567 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:65400 | RHEA:65401 | RHEA:65402 | RHEA:65403 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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| MetaCyc help_outline |
Publications
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Profiling fruit volatiles in the progeny of a 'Royal Gala' x 'Granny Smith' apple (Malus x domestica) cross.
Rowan D.D., Hunt M.B., Dimouro A., Alspach P.A., Weskett R., Volz R.K., Gardiner S.E., Chagne D.
Volatile flavor compounds from the fruit of the progeny of two apple (Malus x domestica) cultivars with distinctive flavor and volatile profiles, 'Royal Gala' and 'Granny Smith', were measured by headspace gas chromatography-mass spectrometry over two fruiting seasons. Principal component analysis ... >> More
Volatile flavor compounds from the fruit of the progeny of two apple (Malus x domestica) cultivars with distinctive flavor and volatile profiles, 'Royal Gala' and 'Granny Smith', were measured by headspace gas chromatography-mass spectrometry over two fruiting seasons. Principal component analysis separated the volatile profiles into two groups according to the amounts produced of butyl, 2-methybutyl, pentyl, and hexyl acetates and of ethyl butanoate, butanol, 2-methylbutanol, and hexanol. Fruit containing the four acetate esters clustered with the 'Royal Gala' parent and were scored more similar to 'Royal Gala' than to "Granny Smith' in flavor. Fruit clustering with the 'Granny Smith' parent contained higher levels of ethyl butanoate and alcohols. Levels of acetate esters correlated to levels of their alcohol precursors, and control of this trait segregated in Mendelian fashion. The locus was mapped to the top of 'Royal Gala' linkage group 2 close to the Rvi4 (Vh4) locus for resistance to Venturia inaequalis , the causal agent of apple scab. << Less
J Agric Food Chem 57:7953-7961(2009) [PubMed] [EuropePMC]
This publication is cited by 12 other entries.
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The AAT1 locus is critical for the biosynthesis of esters contributing to 'ripe apple' flavour in 'Royal Gala' and 'Granny Smith' apples.
Souleyre E.J.F., Chagne D., Chen X., Tomes S., Turner R.M., Wang M.Y., Maddumage R., Hunt M.B., Winz R.A., Wiedow C., Hamiaux C., Gardiner S.E., Rowan D.D., Atkinson R.G.
The 'fruity' attributes of ripe apples (Malus × domestica) arise from our perception of a combination of volatile ester compounds. Phenotypic variability in ester production was investigated using a segregating population from a 'Royal Gala' (RG; high ester production) × 'Granny Smith' (GS; low es ... >> More
The 'fruity' attributes of ripe apples (Malus × domestica) arise from our perception of a combination of volatile ester compounds. Phenotypic variability in ester production was investigated using a segregating population from a 'Royal Gala' (RG; high ester production) × 'Granny Smith' (GS; low ester production) cross, as well as in transgenic RG plants in which expression of the alcohol acyl transferase 1 (AAT1) gene was reduced. In the RG × GS population, 46 quantitative trait loci (QTLs) for the production of esters and alcohols were identified on 15 linkage groups (LGs). The major QTL for 35 individual compounds was positioned on LG2 and co-located with AAT1. Multiple AAT1 gene variants were identified in RG and GS, but only two (AAT1-RGa and AAT1-GSa) were functional. AAT1-RGa and AAT1-GSa were both highly expressed in the cortex and skin of ripe fruit, but AAT1 protein was observed mainly in the skin. Transgenic RG specifically reduced in AAT1 expression showed reduced levels of most key esters in ripe fruit. Differences in the ripe fruit aroma could be perceived by sensory analysis. The transgenic lines also showed altered ratios of biosynthetic precursor alcohols and aldehydes, and expression of a number of ester biosynthetic genes increased, presumably in response to the increased substrate pool. These results indicate that the AAT1 locus is critical for the biosynthesis of esters contributing to a 'ripe apple' flavour. << Less
Plant J. 78:903-915(2014) [PubMed] [EuropePMC]
This publication is cited by 9 other entries.
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An alcohol acyl transferase from apple (cv. Royal Gala), MpAAT1, produces esters involved in apple fruit flavor.
Souleyre E.J.F., Greenwood D.R., Friel E.N., Karunairetnam S., Newcomb R.D.
Apple flavor is characterized by combinations of ester compounds, which increase markedly during fruit ripening. The final step in ester biosynthesis is catalyzed by alcohol acyl transferases (AATs) that use coenzyme A (CoA) donors together with alcohol acceptors as substrates. The gene MpAAT1, wh ... >> More
Apple flavor is characterized by combinations of ester compounds, which increase markedly during fruit ripening. The final step in ester biosynthesis is catalyzed by alcohol acyl transferases (AATs) that use coenzyme A (CoA) donors together with alcohol acceptors as substrates. The gene MpAAT1, which produces a predicted protein containing features of other plant acyl transferases, was isolated from Malus pumila (cv. Royal Gala). The MpAAT1 gene is expressed in leaves, flowers and fruit of apple. The recombinant enzyme can utilize a range of alcohol substrates from short to medium straight chain (C3-C10), branched chain, aromatic and terpene alcohols. The enzyme can also utilize a range of short to medium chain CoAs. The binding of the alcohol substrate is rate limiting compared with the binding of the CoA substrate. Among different alcohol substrates there is more variation in turnover compared with K(m) values. MpAAT1 is capable of producing many esters found in Royal Gala fruit, including hexyl esters, butyl acetate and 2-methylbutyl acetate. Of these, MpAAT1 prefers to produce the hexyl esters of C3, C6 and C8 CoAs. For the acetate esters, however, MpAAT1 preference depends upon substrate concentration. At low concentrations of alcohol substrate the enzyme prefers utilizing the 2-methylbutanol over hexanol and butanol, while at high concentrations of substrate hexanol can be used at a greater rate than 2-methylbutanol and butanol. Such kinetic characteristics of AATs may therefore be another important factor in understanding how the distinct flavor profiles of different fruit are produced during ripening. << Less
FEBS J. 272:3132-3144(2005) [PubMed] [EuropePMC]
This publication is cited by 10 other entries.