Reaction participants Show >> << Hide
- Name help_outline 4-prenylphlorisovalerophenone Identifier CHEBI:134341 Charge 0 Formula C16H22O4 InChIKeyhelp_outline LWLGKGHHVBVDKB-UHFFFAOYSA-N SMILEShelp_outline OC1=C(C(O)=C(C(O)=C1)CC=C(C)C)C(=O)CC(C)C 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 dimethylallyl diphosphate Identifier CHEBI:57623 (Beilstein: 5288443; CAS: 22679-02-3) help_outline Charge -3 Formula C5H9O7P2 InChIKeyhelp_outline CBIDRCWHNCKSTO-UHFFFAOYSA-K SMILEShelp_outline CC(C)=CCOP([O-])(=O)OP([O-])([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 77 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline deoxyhumulone Identifier CHEBI:134345 (CAS: 4374-93-0) help_outline Charge 0 Formula C21H30O4 InChIKeyhelp_outline NQYBQBZOHCACCR-UHFFFAOYSA-N SMILEShelp_outline C1(O)=C(CC=C(C)C)C(=C(C(O)=C1CC=C(C)C)C(=O)CC(C)C)O 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 diphosphate Identifier CHEBI:33019 (Beilstein: 185088) help_outline Charge -3 Formula HO7P2 InChIKeyhelp_outline XPPKVPWEQAFLFU-UHFFFAOYSA-K SMILEShelp_outline OP([O-])(=O)OP([O-])([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 1,085 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:51784 | RHEA:51785 | RHEA:51786 | RHEA:51787 | |
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| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Related reactions help_outline
More general form(s) of this reaction
Publications
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A heteromeric membrane-bound prenyltransferase complex from hop catalyzes three sequential aromatic prenylations in the bitter Acid pathway.
Li H., Ban Z., Qin H., Ma L., King A.J., Wang G.
Bitter acids (α and β types) account for more than 30% of the fresh weight of hop (Humulus lupulus) glandular trichomes and are well known for their contribution to the bitter taste of beer. These multiprenylated chemicals also show diverse biological activities, some of which have potential benef ... >> More
Bitter acids (α and β types) account for more than 30% of the fresh weight of hop (Humulus lupulus) glandular trichomes and are well known for their contribution to the bitter taste of beer. These multiprenylated chemicals also show diverse biological activities, some of which have potential benefits to human health. The bitter acid biosynthetic pathway has been investigated extensively, and the genes for the early steps of bitter acid synthesis have been cloned and functionally characterized. However, little is known about the enzyme(s) that catalyze three sequential prenylation steps in the β-bitter acid pathway. Here, we employed a yeast (Saccharomyces cerevisiae) system for the functional identification of aromatic prenyltransferase (PT) genes. Two PT genes (HlPT1L and HlPT2) obtained from a hop trichome-specific complementary DNA library were functionally characterized using this yeast system. Coexpression of codon-optimized PT1L and PT2 in yeast, together with upstream genes, led to the production of bitter acids, but no bitter acids were detected when either of the PT genes was expressed by itself. Stepwise mutation of the aspartate-rich motifs in PT1L and PT2 further revealed the prenylation sequence of these two enzymes in β-bitter acid biosynthesis: PT1L catalyzed only the first prenylation step, and PT2 catalyzed the two subsequent prenylation steps. A metabolon formed through interactions between PT1L and PT2 was demonstrated using a yeast two-hybrid system, reciprocal coimmunoprecipitation, and in vitro biochemical assays. These results provide direct evidence of the involvement of a functional metabolon of membrane-bound prenyltransferases in bitter acid biosynthesis in hop. << Less
Plant Physiol. 167:650-659(2015) [PubMed] [EuropePMC]
This publication is cited by 12 other entries.