H-Trp-OH | Tryptophan | Indoles

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Quality Control of H-Trp-OH Purity: 98% SDS Specification

COA

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NMR

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CNMR

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HPLC

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LC-MS

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Product Citations

Rebamipide and Derivatives are Potent, Selective Inhibitors of Histidine Phosphatase Activity of the Suppressor of T Cell Receptor Signaling Proteins

Faisal Aziz ; Kanamata Reddy ; Virneliz Fernandez Vega ; Raja Dey ; Katherine A. Hicks ; Sumitha Rao , et al.

DOI: 10.1021/acs.jmedchem.3c01763 JMC,2024,67(3):1949-1960.

Abstract: The suppressor of T cell receptor signaling (Sts) proteins are negative regulators of immune signaling. Genetic inactivation of these proteins leads to significant resistance to infection. From a 590,000 compound high-throughput screen, we identified the 2-(1H)-quinolinone derivative, rebamipide, as a putative inhibitor of Sts phosphatase activity. Rebamipide, and a small library of derivatives, are competitive, selective inhibitors of Sts-1 with IC50 values from low to submicromolar. SAR analysis indicates that the quinolinone, the acid, and the amide moieties are all essential for activity. A crystal structure confirmed the SAR and reveals key interactions between this class of compound and the protein. Although rebamipide has poor cell permeability, we demonstrated that a liposomal preparation can inactivate the phosphatase activity of Sts-1 in cells. These studies demonstrate that Sts-1 enzyme activity can be pharmacologically inactivated and provide foundational tools and insights for the development of immune-enhancing therapies that target the Sts proteins.

Purchased from AmBeed: 2251-65-2 ; 90098-04-7 ; 4876-14-6 ; 90098-08-1 ; 874-60-2 ; 4876-10-2 ; 7158-32-9 ; 5271-67-0 ; 118-45-6 ; 73-22-3 ; 56-41-7 ; 34893-92-0 ; 403-43-0 ; 58757-38-3 ; 76903-88-3 ; 52-90-4 ; 6068-72-0 ; 4122-68-3 ; 2243-83-6 ; 38818-50-7 ; 16331-45-6 ; 36823-88-8 ; 90098-06-9 ; 90098-05-8 ; 3024-72-4 ; 618-46-2 ; 63024-43-1 ; 22980-09-2 ; 681806-75-7 ; 39544-74-6

Product Details of H-Trp-OH

CAS No. :	73-22-3
Formula :	C₁₁H₁₂N₂O₂
M.W :	204.23
SMILES Code :	N[C@@H](CC1=CNC2=CC=CC=C12)C(O)=O
Synonyms :	Tryptophan; Tryptophane; L-Tryptophane
MDL No. :	MFCD00064340
InChI Key :	QIVBCDIJIAJPQS-VIFPVBQESA-N
Pubchem ID :	6305

Safety of H-Trp-OH

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Application In Synthesis of H-Trp-OH

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 73-22-3 ]

[ 73-22-3 ] Synthesis Path-Downstream 1~25

1
[ 64-17-5 ]
[ 73-22-3 ]
[ 6519-67-1 ]

References: [1]Journal of Biological Chemistry,1930,vol. 85,p. 209.

2
[ 16108-03-5 ]
[ 73-22-3 ]
[ 38854-43-2 ]

References: [1]Patent: US2511867,1948,A .
[2]Patent: DE814296,1949,C .
    DRP/DRBP Org.Chem.,.
    DRP/DRBP Org.Chem.,.
[3]Patent: DE814296,1949,C .
    DRP/DRBP Org.Chem.,.
    DRP/DRBP Org.Chem.,.

3
[ 47355-10-2 ]
[ 73-22-3 ]

References: [1]Journal of the Chemical Society. Chemical communications,1991,p. 530 - 531.
[2]Chemical and pharmaceutical bulletin,1987,vol. 35,p. 3447 - 3452.

4
[ 66065-85-8 ]
[ 73-22-3 ]
[ 88050-14-0 ]

References: [1]Synthesis,1983,p. 671 - 673.

5
[ 2418-95-3 ]
[ 2799-07-7 ]
[ 4727-00-8 ]
[ 108-24-7 ]
[ 73-22-3 ]
Cys-D-Phe-resin [ No CAS ]
(4R,7S,10S,13S,16R,19R)-19-Acetylamino-10-(4-amino-butyl)-16-benzyl-7-(4-hydroxy-benzyl)-13-(1H-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaaza-cycloicosane-4-carboxylic acid amide [ No CAS ]