Reaction participants Show >> << Hide
- Name help_outline L-kynurenine Identifier CHEBI:57959 Charge 0 Formula C10H12N2O3 InChIKeyhelp_outline YGPSJZOEDVAXAB-QMMMGPOBSA-N SMILEShelp_outline Nc1ccccc1C(=O)C[C@H]([NH3+])C([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 34 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline L-tryptophan Identifier CHEBI:57912 Charge 0 Formula C11H12N2O2 InChIKeyhelp_outline QIVBCDIJIAJPQS-VIFPVBQESA-N SMILEShelp_outline [NH3+][C@@H](Cc1c[nH]c2ccccc12)C([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 63 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:71183 | RHEA:71184 | RHEA:71185 | RHEA:71186 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
|
Related reactions help_outline
More general form(s) of this reaction
Publications
-
Nanosensor detection of an immunoregulatory tryptophan influx/kynurenine efflux cycle.
Kaper T., Looger L.L., Takanaga H., Platten M., Steinman L., Frommer W.B.
Mammalian cells rely on cellular uptake of the essential amino acid tryptophan. Tryptophan sequestration by up-regulation of the key enzyme for tryptophan degradation, indoleamine 2,3-dioxygenase (IDO), e.g., in cancer and inflammation, is thought to suppress the immune response via T cell starvat ... >> More
Mammalian cells rely on cellular uptake of the essential amino acid tryptophan. Tryptophan sequestration by up-regulation of the key enzyme for tryptophan degradation, indoleamine 2,3-dioxygenase (IDO), e.g., in cancer and inflammation, is thought to suppress the immune response via T cell starvation. Additionally, the excreted tryptophan catabolites (kynurenines) induce apoptosis of lymphocytes. Whereas tryptophan transport systems have been identified, the molecular nature of kynurenine export remains unknown. To measure cytosolic tryptophan steady-state levels and flux in real time, we developed genetically encoded fluorescence resonance energy transfer nanosensors (FLIPW). The transport properties detected by FLIPW in KB cells, a human oral cancer cell line, and COS-7 cells implicate LAT1, a transporter that is present in proliferative tissues like cancer, in tryptophan uptake. Importantly, we found that this transport system mediates tryptophan/kynurenine exchange. The tryptophan influx/kynurenine efflux cycle couples tryptophan starvation to elevation of kynurenine serum levels, providing a two-pronged induction of apoptosis in neighboring cells. The strict coupling protects cells that overproduce IDO from kynurenine accumulation. Consequently, this mechanism may contribute to immunosuppression involved in autoimmunity and tumor immune escape. << Less
PLoS Biol 5:e257-e257(2007) [PubMed] [EuropePMC]
This publication is cited by 2 other entries.