131831-87-3

Basic information

• Product Name: D-Tryptophan, N-methyl-, methyl ester
• Synonyms: N-Me-D-Trp-OMe
• CAS NO: 131831-87-3
• Molecular Formula: C13H16N2O2
• Molecular Weight: 232.282
• Mol File: 131831-87-3.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: D-Tryptophan, N-methyl-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: D-Tryptophan, N-methyl-, methyl ester(131831-87-3)
• EPA Substance Registry System: D-Tryptophan, N-methyl-, methyl ester(131831-87-3)

Safety Data

• Hazardous Substances Data: 131831-87-3(Hazardous Substances Data)

Usage

Description

D-Tryptophan, N-methyl-, methyl ester is an organic compound that serves as an intermediate in the synthesis of Jasplakinolide (J210700), a potent inhibitor of prostate and breast carcinoma cell proliferation. It is characterized by its unique molecular structure, which includes a tryptophan backbone with a methyl group attached to the nitrogen atom and a methyl ester group attached to the carboxylic acid.

Uses

Used in Pharmaceutical Industry:
D-Tryptophan, N-methyl-, methyl ester is used as a key intermediate in the synthesis of Jasplakinolide (J210700) for its potential anticancer properties. It plays a crucial role in the development of new therapeutic agents targeting prostate and breast carcinoma cell proliferation, offering a promising avenue for cancer treatment and research.

Upstream product

• 2258-42-6 formyl acetic anhydride 
• 4299-70-1 D-Tryptophan methyl ester 
• 14907-27-8 (R)-(+)-tryptophan methyl ester hydrochloride 
• 122747-97-1 methyl (R)-3-(1H-indol-3-yl)-2-(N-tert-butoxycarbonyl-N-methylamino)propanoate 
• 134781-88-7 D-N-formyl tryptophan methyl ester 

Downstream Products

• 134815-49-9 (E)-(2S,6R,8S)-8-<(tert-Butyldimethylsilyl)oxy>-2,4,6-trimethyl-4-nonenoyl-(S)-alanyl-N-methyl-2-bromo-(R)-tryptophanyl-O-methyl-(R)-β-tyrosine Methyl Ester 
• 161925-59-3 jaspamide Z₁ 
• 134781-91-2 (R)-3-[(R)-2-[((S)-2-Amino-propionyl)-methyl-amino]-3-(2-bromo-1H-indol-3-yl)-propionylamino]-3-(4-methoxy-phenyl)-propionic acid methyl ester 
• 131791-80-5 N-Boc-(S)-alanyl-N-methyl-2-bromo-(R)-tryptophanyl-O-methyl-(R)-β-tyrosine Methyl Ester 
• 119717-37-2 jasplakinolide 
• 873326-29-5 N-[(2S)-3-(3-{(2R)-2-[(tert-butoxycarbonyl)amino]propyl}phenyl)-2-methylpropanoyl]-L-alanyl-N-[(1R)-3-tert-butoxy-1-(4-methoxyphenyl)-3-oxopropyl]-N-methyl-D-tryptophanamide 
• 873326-28-4 N-(tert-butoxycarbonyl)-L-alanyl-N-[(1R)-3-tert-butoxy-1-(4-methoxyphenyl)-3-oxopropyl]-N-methyl-D-tryptophanamide 
• 873326-33-1 L-alanyl-N-[(1R)-3-tert-butoxy-1-(4-methoxyphenyl)-3-oxopropyl]-N-methyl-D-tryptophanamide 

Relevant articles and documents

Synthesis of simplified halogenated chondramide derivatives with strong cytostatic properties

Removing the methyl groups and the stereogenic centers from the ω-hydroxy acid of the chondramides results in a significant drop in the cytotoxicity of these interesting depsipeptides. This effect can be almost compensated for by introduction of a second

Chondramide C: Synthesis, configurational assignment, and structure-activity relationship studies

(Chemical Equation Presented) Two solutions for one problem: Of the four isomers of chondramide C synthesized, the two shown in the scheme exhibit nearly the same conformation of the peptide segment and consequently unfold equal biological activities.

Self-Reproduction of Chirality. Asymmetric Synthesis of β-Aryl-β-amino Acids from Enantiomerically Pure Dihydropyrimidinones

Enantiomerically pure dihydropyrimidinone 1 reacts with aryl iodides in the presence of catalytic amounts of Pd(OAc)2 and added phosphine to afford dihydropyrimidinone 4, in which a formal conjugate addition of the aryl group to the α,β-unsaturated system