Rhea - reaction knowledgebase

Enzymes

UniProtKB

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Name ^help_outline N-benzoyl-L-phenylalaninol Identifier CHEBI:145107 (CAS: 4503-96-2) ^help_outline Charge 0 Formula C16H17NO2 InChIKey^help_outline RFYNAVYPYXLVOM-HNNXBMFYSA-N SMILES^help_outline C([C@H](CC1=CC=CC=C1)NC(=O)C=2C=CC=CC2)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 benzoate Identifier CHEBI:16150 (CAS: 766-76-7) ^help_outline Charge -1 Formula C7H5O2 InChIKey^help_outline WPYMKLBDIGXBTP-UHFFFAOYSA-M SMILES^help_outline [O-]C(=O)c1ccccc1 2D coordinates Mol file for the small molecule Search links Involved in 17 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name ^help_outline L-phenylalanine Identifier CHEBI:58095 Charge 0 Formula C9H11NO2 InChIKey^help_outline COLNVLDHVKWLRT-QMMMGPOBSA-N SMILES^help_outline [NH3+][C@@H](Cc1ccccc1)C([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 74 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name ^help_outline ATP Identifier CHEBI:30616 (Beilstein: 3581767) ^help_outline Charge -4 Formula C10H12N5O13P3 InChIKey^help_outline ZKHQWZAMYRWXGA-KQYNXXCUSA-J SMILES^help_outline Nc1ncnc2n(cnc12)[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 1,284 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name ^help_outline asperphenamate Identifier CHEBI:145105 (CAS: 63631-36-7) ^help_outline Charge 0 Formula C32H30N2O4 InChIKey^help_outline CVULDJMCSSACEO-VMPREFPWSA-N SMILES^help_outline C=1C(=CC=CC1)C(=O)N[C@H](COC([C@H](CC=2C=CC=CC2)NC(C=3C=CC=CC3)=O)=O)CC=4C=CC=CC4 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 AMP Identifier CHEBI:456215 Charge -2 Formula C10H12N5O7P InChIKey^help_outline UDMBCSSLTHHNCD-KQYNXXCUSA-L SMILES^help_outline Nc1ncnc2n(cnc12)[C@@H]1O[C@H](COP([O-])([O-])=O)[C@@H](O)[C@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 512 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 InChIKey^help_outline XPPKVPWEQAFLFU-UHFFFAOYSA-K SMILES^help_outline OP([O-])(=O)OP([O-])([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 1,139 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 9,521 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule

Cross-references

	RHEA:61908	RHEA:61909	RHEA:61910	RHEA:61911
Reaction direction	undefined	left-to-right	right-to-left	bidirectional
UniProtKB ^help_outline	1 proteins	1 proteins

Publications

Asperphenamate biosynthesis reveals a novel two-module NRPS system to synthesize amino acid esters in fungi.

Li W., Fan A., Wang L., Zhang P., Liu Z., An Z., Yin W.B.

Amino acid esters are a group of structurally diverse natural products with distinct activities. Some are synthesized through an inter-molecular esterification step catalysed by nonribosomal peptide synthetase (NRPS). In bacteria, the formation of the intra-molecular ester bond is usually catalyse ... >> More

Amino acid esters are a group of structurally diverse natural products with distinct activities. Some are synthesized through an inter-molecular esterification step catalysed by nonribosomal peptide synthetase (NRPS). In bacteria, the formation of the intra-molecular ester bond is usually catalysed by a thioesterase domain of NRPS. However, the mechanism by which fungal NRPSs perform this process remains unclear. Herein, by targeted gene disruption in <i>Penicillium brevicompactum</i> and heterologous expression in <i>Aspergillus nidulans</i>, we show that two NRPSs, ApmA and ApmB, are sufficient for the synthesis of an amino acid ester, asperphenamate. Using the heterologous expression system, we identified that ApmA, with a reductase domain, rarely generates dipeptidyl alcohol. In contrast, ApmB was determined to not only catalyse inter-molecular ester bond formation but also accept the linear dipeptidyl precursor into the NRPS chain. The mechanism described here provides an approach for the synthesis of new small molecules with NRPS as the catalyst. Our study reveals for the first time a two-module NRPS system for the formation of amino acid esters in nature. << Less

Chem. Sci. 9:2589-2594(2018) [PubMed] [EuropePMC]

This publication is cited by 1 other entry.

Comments

This reaction starts by the ligation of the substrates to the carrier domain of the NRPS (nonribosomal peptide synthetase). The route followed in similar reactions, involves the activation of the substrate by adenylation, this is the reason the reaction includes ATP hydrolysis to AMP and diphosphate.