2717-76-2

Usage

Uses

Used in Neurotransmitter Receptor Studies:
Z-TRP-OME is used as a research compound for studying neurotransmitter receptors. Its unique structure allows for the exploration of the interactions between neurotransmitters and their receptors, providing insights into the mechanisms of neurotransmission and potential targets for drug development.
Used in Peptide Structure-Activity Relationship Studies:
In the field of peptide research, Z-TRP-OME serves as a key component in understanding the relationship between peptide structure and biological activity. Its modified properties enable researchers to examine the effects of structural changes on peptide function and activity, contributing to the design of more effective peptide-based therapeutics.
Used in the Synthesis of Novel Peptidomimetics:
Z-TRP-OME is utilized as a building block in the synthesis of novel peptidomimetics. Its unique structure and properties facilitate the development of peptidomimetics that mimic the biological activity of peptides, offering potential applications in drug discovery and therapeutic interventions.
Used in Chemical and Laboratory Research:
Z-TRP-OME is employed as a reagent in various chemical and laboratory research applications. Its modified tryptophan structure provides a versatile platform for studying the chemical properties of amino acids and their derivatives, contributing to the advancement of chemical knowledge and the development of new synthetic methods.

Upstream product

• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 
• 501-53-1 benzyl chloroformate 
• 186581-53-3 diazomethane 
• 7432-21-5 N-carbobenzyloxy-L-tryptophane 
• 120-72-9 indole 
• 104597-98-0 (S)-2-methoxycarbonyl-1-benzyloxycarbonylaziridine 
• 73-22-3 L-Tryptophan 
• 67-56-1 methanol 
• 4299-70-1 L-tryptophan methyl ester 
• 1053208-94-8 N-carbobenzyloxy-2-iodo-L-tryptophan methyl ester 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 74-88-4 methyl iodide 

Downstream Products

• 1053209-02-1 N-carbobenzyloxy-1-acetyl-L-tryptophan methyl ester 
• 1352815-90-7 C₃₁H₂₄N₄O₅ 
• 22839-13-0 benzyl (S)-(1-hydrazinyl-3-(1H-indol-3-yl)-1-oxopropan-2-yl)carbamate 
• 146645-63-8 (2S)-2-amino-3-(1-tert-butoxycarbonylindol-3-yl)propanoic acid 
• 143824-78-6 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester 
• 131442-94-9 (S,S)-(2-(4-((1-(((phenylmethyl)oxy)carbonyl)-2-methylpropyl)amino)-1H-indol-3-yl)-1-(hydroxymethyl)ethyl)carbamic acid, phenylmethyl ester 
• 110815-27-5 (S)-(2-acetoxy)-1-((1H-indol-3-ylmethyl)ethyl)carbamic acid, phenylmethyl ester 
• 84590-48-7 (+)-Epi-indolactam-V 
• 110815-33-3 2-[3-((S)-2-Benzyloxycarbonylamino-3-hydroxy-propyl)-1H-indol-4-ylamino]-3-methyl-butyric acid 2,5-dioxo-pyrrolidin-1-yl ester 
• 110815-30-0 Acetic acid (R)-2-benzyloxycarbonylamino-3-(6-nitro-1H-indol-3-yl)-3-oxo-propyl ester 
• 110815-29-7 Acetic acid (R)-2-benzyloxycarbonylamino-3-(4-nitro-1H-indol-3-yl)-3-oxo-propyl ester 
• 110815-31-1 Acetic acid (R)-3-(4-amino-1H-indol-3-yl)-2-benzyloxycarbonylamino-3-oxo-propyl ester 
• 110815-28-6 (R)-(1-((acetoxy)methyl)-2-(1H-indol-3-yl)-2-oxoethyl)carbamic acid phenylmethyl ester 
• 110815-32-2 (S)-(2-(4-amino-1H-indol-3-yl)-1-(hydroxymethyl)ethyl)carbamic acid, phenylmethyl ester 

Relevant academic research and scientific papers

Method for preparing pharmaceutical intermediate of tryptophan derivative

The synthesis method comprises the following steps: L - tryptophan derivatives are taken as starting materials, and esterification is carried out in sequence. The amidation, Boc protection, hydrolysis, amidation or sequential esterification, amidation, Boc protection, hydrogenation, hydrolysis, amidation yields a target product, a tryptophan derivative pharmaceutical intermediate. The preparation method has the advantages of cheap and easily available raw materials, environment friendliness, less process three wastes, accords with the idea of green pharmacy, mild reaction conditions, simple process, simple and convenient operation, high yield and purity and easy amplification and production.

An efficient, stereocontrolled and versatile synthetic route to bicyclic partially saturated privileged scaffolds

Herein, we describe the development of a simple, high yielding and stereocontrolled strategy for the synthesis of a series of triazolopiperazines and other biologically relevant fused scaffolds from optically active amino acids. This route was applied to the synthesis of 22 scaffolds containing new, previously inaccessible vectors and used to access a novel analogue of ganaplacide.

Synthesis of tryptophans by Lewis acid promoted ring-opening of aziridine-2-carboxylates: Optimization of protecting group and Lewis acid

The preparation of tryptophan derivatives through the Lewis acid promoted substitution of aziridine carboxylates with indole was found to be accompanied by a ring-expansion reaction to generate an oxazolidinone byproduct. The ratio of tryptophan to oxazol

Aerobic palladium(II)-catalyzed 5-endo-trig cyclization: An entry into the diastereoselective C-2 alkenylation of indoles with tri- and tetrasubstituted double bonds

The endo trick: An endo ring closure onto the trigonal β carbon atom of α,β-unsaturated acceptors that are tethered to the indole nitrogen atom followed by amide cleavage enables the diastereoselective C-2 alkenylation of indoles with fully substituted double bonds. The carboxy group functions as a synthetically useful temporary tether (see scheme). Copyright

Orthogonal protecting groups in the synthesis of tryptophanyl- hexahydropyrroloindoles

The synthesis of various polycyclic systems containing aC 3a-Ni bond between a hexahydropyrrolo[2,3-b]indole and an indole tryptophan is described here. A series of experiments were performed to determine the best combination of five orthogonal protecting groups and the best reaction conditions for formation of said bond, which is a common feature among many recently discovered marine natural products.

A favorable, narrow, δh Hansen-parameter domain for gelation of low-molecular-weight amino acid derivatives

In recent years, the design of new low-molecular-weight gelators (LMWGs) has attracted considerable attention because of the interesting supramolecular architectures as well as industrial applications. In this context, the role of the organic solvent in d

NOVEL TRICYCLIC CHIRAL COMPOUNDS AND THEIR USE IN ASYMMETRIC CATALYSIS

The present invention relates to a compound of general Formula (XX), its formation and its use in asymmetric catalysis. In Formula (XX) R and R31 are independently —COOR3, —R4COOR3, —R4CHO, —R4COR3, —R4CONR5R6, —R4COX, —R4OP(═O)(OH)2, —R4P(═O)(OH)2), —R4C(O)C(R3)CR5R6 and —R4CO2COR3. In addition, R31 may also be hydrogen. R3, R5 and R6 are independently hydrogen, an aliphatic group with a main chain having 1 to about 20 carbon atoms, an alicyclic group, an aromatic group, an arylaliphatic group or an arylalicyclic group, comprising 0 to about 3 heteroatoms independently selected from the group consisting of N, O, S, Se and Si. R4 an aliphatic bridge with a main chain having 1 to about 20 carbon atoms, an alicyclic bridge, an aromatic bridge, an arylaliphatic bridge or an arylalicyclic bridge, comprising 0 to about 3 heteroatoms independently selected from the group consisting of N, O, S, Se and Si, and X is halogen. In Formula (XX) R30 is —C(OH)R1R2 or —COOR14, wherein R1, R2 and R14 are independently hydrogen, an aliphatic group with a main chain having 1 to about 20 carbon atoms, an alicyclic group, an aromatic group, an arylaliphatic group or an arylalicyclic group, comprising 0 to about 3 heteroatoms independently selected from the group consisting of N, O, S, Se and Si.

Hexahydropyrrolo [2,3-b]indoles: A new class of structurally rigid tricyclic skeleton for oxazaborolidine-catalyzed asymmetric borane reduction

A new class of structurally rigid tricyclic chiral ligands based on the hexahydropyrrolo [2,3b]indole skeleton has been rationally designed and the catalytic abilities in asymmetric catalysis have been shown in the enantioselective borane reduction of prochiral ketones to afford the chiral alcohols in excellent yields and high enantioselectivities (up to 97% ee).

Synthesis of a β-tetrapeptide analog as a mother compound for the development of matrix metalloproteinase-2-imaging agents

Matrix metalloproteinase-2 (MMP-2) is an attractive target for the diagnosis of cancer and atherosclerosis in nuclear imaging. A cyclic decapeptide, cCTTHWGFTLC (cCTT), has been used as the mother compound for the development of MMP-2-imaging agents with high potency and selectivity. Most of radiolabeled derivatives of cCTT currently developed for in vivo studies of MMP-2, however, suffer from low accumulation in the target tissues, such as tumors. For enhanced in vivo stability and tissue penetration, we designed a linear β-tetrapeptide analog, H-β3-Phe-β-Ala- β3-Trp-β3-His-OH (1), to mimic cCTT. The component β-amino acids were prepared by reduction of N-protected α-amino acid methyl esters to the alcohols, followed by conversion into the cyanides, and subsequent hydrolysis. Compound 1 was obtained from these β-amino acids by the conventional solution method. In MMP-2 inhibition assay, compound 1 displayed desirably significant inhibition, which was comparable to cCTT. These findings suggest that compound 1 may serve as a mother compound in the design and development of in vivo MMP-2-imaging agents.

Unexpected domino ring closure: highly stereoselective construction of a tetracyclic indole alkaloid ring system

An unexpected highly stereoselective domino ring closure gave the tetracyclic indole alkaloid IV-2 in good yield in one hydrogenation step. Crown Copyright