17430-65-8

Basic information

• Product Name: Z-VAL-TRP-OME
• Synonyms: Z-VAL-TRP-OME
• CAS NO: 17430-65-8
• Molecular Formula: C₂₅H₂₉N₃O₅
• Molecular Weight: 451.51
• Mol File: 17430-65-8.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Storage Temp.: -15°C
• CAS DataBase Reference: Z-VAL-TRP-OME(CAS DataBase Reference)
• NIST Chemistry Reference: Z-VAL-TRP-OME(17430-65-8)
• EPA Substance Registry System: Z-VAL-TRP-OME(17430-65-8)

Safety Data

• Hazardous Substances Data: 17430-65-8(Hazardous Substances Data)

Usage

General Description

Z-VAL-TRP-OME is a chemical compound consisting of three amino acids - valine, tryptophan, and omethionine - that are linked together. It is commonly used in research as a selective antagonist of the 5-HT1A receptor, which is involved in the regulation of serotonin levels in the brain. Z-VAL-TRP-OME has been studied for its potential therapeutic effects in various conditions such as anxiety, depression, and addiction. It is also being investigated for its role in modulating pain perception and behavior. Overall, Z-VAL-TRP-OME has shown promising potential as a tool for understanding the neurological mechanisms underlying mood disorders and as a potential target for the development of new therapeutic agents.

Upstream product

• 1149-26-4 (S)-N-(benzyloxycarbonyl)valine 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 
• 4299-70-1 L-tryptophan methyl ester 

Downstream Products

• 1244546-14-2 (S)-methyl 2-(1-benzyloxycarbonylamino-2-methylpropyl)-5-(indol-3-yl)-oxazole-4-carboxylate 

Relevant articles and documents

Gold-catalyzed direct alkynylation of tryptophan in peptides using TIPS-EBX

The selective functionalization of peptides containing only natural amino acids is important for the modification of biomolecules. In particular, the installation of an alkyne as a useful handle for bioconjugation is highly attractive, but the use of a carbon linker is usually required. Herein, we report the gold-catalyzed direct alkynylation of tryptophan in peptides using the hypervalent iodine reagent TIPS-EBX (1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one). The reaction proceeded in 50-78% yield under mild conditions and could be applied to peptides containing other nucleophilic and aromatic amino acids, such as serine, phenylalanine or tyrosine.

Conformational effects in reversed-phase liquid chromatographic separation of diastereomers of cyclic dipeptides

The capacity factors, k′, of 11 cyclic dipeptides (X-Y) including diastereomers have been determined on an RP-HPLC column in 30% and 50% methanol and 10%, 30%, and 50% acetonitrile solutions. These factors are roughly correlated with hydrophobic parameters, such as octanol-water partition coefficients estimated and k′ values for alcohols. For a pair of diastereomers of cyclic (L-X-L-Phe) and (L-X-D-Phe) derivatives k′LL is larger than k′LD and for cyclic (D-Ala-L-Trp) and (L-Ala-L-Trp) k′LL is smaller than k′DL, particularly in highly aqueous solutions. These elution orders can be well predicted by the holistic molecular surface area approach which takes into account the folded structures of cyclic dipeptides. The present results will be useful for prediction of the log k′ values of larger peptides and the hydrophobicity and related properties of peptides.