2279-15-4

Basic information

• Product Name: N-Cbz-D-Tryptophan
• Synonyms: Z-D-TRP-OH;Z-D-TRYPTOPHAN;N-CARBOBENZOXY-D-TRYPTOPHAN;N(ALPHA)-CBZ-D-TRYPTOPHAN;N(ALPHA)-BENZYLOXYCARBONYL-D-TRYPTOPHAN;N-ALPHA-CARBOBENZOXY-D-TRPTOPHAN;CBZ-D-TRP-OH;CBZ-D-TRYPTOPHAN
• CAS NO: 2279-15-4
• Molecular Formula: C₁₉H₁₈N₂O₄
• Molecular Weight: 338.36
• EINECS: 1533716-785-6
• Product Categories: PROTECTED AMINO ACID & PEPTIDES;Tryptophan [Trp, W];Z-Amino Acids and Derivatives;Amino Acids;Amino Acids (N-Protected);Biochemistry;Cbz-Amino Acids;Indoles;Tryptophans;Cbz-Amino acid series
• Mol File: 2279-15-4.mol
• Article Data: 9

Chemical Properties

• Melting Point: 122-124°C
• Boiling Point: 619.1 °C at 760 mmHg
• Flash Point: 328.2 °C
• Appearance: /
• Density: 1.341 g/cm³
• Vapor Pressure: 3.46E-16mmHg at 25°C
• Refractive Index: 11 ° (C=1, MeOH)
• Storage Temp.: Store at RT.
• Solubility: soluble in Methanol
• PKA: 3.98±0.10(Predicted)
• BRN: 96744
• CAS DataBase Reference: N-Cbz-D-Tryptophan(CAS DataBase Reference)
• NIST Chemistry Reference: N-Cbz-D-Tryptophan(2279-15-4)
• EPA Substance Registry System: N-Cbz-D-Tryptophan(2279-15-4)

Safety Data

• Statements: 22/22-36/37/38
• Safety Statements: 22-24/25-44-35-28-7-4
• HazardClass: IRRITANT
• Hazardous Substances Data: 2279-15-4(Hazardous Substances Data)

Usage

Description

N-Cbz-D-Tryptophan, also known as Nα-Cbz-D-tryptophan, is an N-Cbz-protected form of D-Tryptophan (T947205). D-Tryptophan is an unnatural isomer of L-Tryptophan (T947210) and is classified as an essential amino acid. It plays a significant role in various biological processes and has potential applications in the pharmaceutical industry due to its unique properties.

Uses

Used in Pharmaceutical Industry:
N-Cbz-D-Tryptophan is used as a building block for the synthesis of various pharmaceutical compounds. Its application is primarily due to its status as an essential amino acid, which can be incorporated into the structure of different drugs to enhance their efficacy or modify their properties.
Used in Synthesis of Oxytocin Antagonists:
N-Cbz-D-Tryptophan is used as a key component in the synthesis of potent Oxytocin antagonists. These antagonists are crucial in the treatment of preterm labor, as they help regulate the hormone levels and prevent premature birth.
Used in Research and Development:
N-Cbz-D-Tryptophan is also utilized in research and development for studying the properties and functions of D-amino acids. Its unique structure allows scientists to explore new avenues in drug design and development, potentially leading to the discovery of novel therapeutic agents.

InChI:InChI=1/C19H18N2O4/c22-18(23)17(10-14-11-20-16-9-5-4-8-15(14)16)21-19(24)25-12-13-6-2-1-3-7-13/h1-9,11,17,20H,10,12H2,(H,21,24)(H,22,23)/t17-/m1/s1

Upstream product

• 501-53-1 benzyl chloroformate 
• 13058-16-7 N-[(phenylmethoxy)carbonyl]-DL-tryptophan 
• 64-17-5 ethanol 
• 62-53-3 aniline 
• 73-22-3 L-tryptophan 
• 75819-24-8 3-benzyloxycarbonyl-2-oxazolone 
• 153-94-6 D-tryptophan 

Downstream Products

• 20696-68-8 N-(N^α-benzyloxycarbonyl-D-tryptophyl)-L-tyrosin-amide 
• 153-94-6 D-tryptophan 
• 96838-37-8 methyl (S)-2-benzyloxycarbonylamino-3-((RS)-2-oxo-3-indolinyl)propanoate 
• 74992-61-3 (S)-1-[2-Benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionyl]-pyrrolidine-2-carboxylic acid 4-nitro-phenyl ester 
• 74992-61-3 (S)-1-[2-Benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionyl]-pyrrolidine-2-carboxylic acid 4-nitro-phenyl ester 
• 74992-65-7 N-carbobenzyloxy-D-tryptophanyl-L-proline p-nitrophenyl ester 
• 81444-73-7 N-(benzyloxycarbonyl)-D-tryptophanyl-L-tryptophan methyl ester 
• 81444-74-8 N-(benzyloxycarbonyl)-D-tryptophanyl-D-tryptophan methyl ester 
• 92421-75-5 N-carbobenzyloxy-D-tryptophan-L-proline methyl ester 
• 111237-81-1 N^α-(benzyloxycarbonyl)-D-tryptophanylarginine methyl ester hydrochloride 
• 108827-29-8 Z-D-Trp-Lys(Boc)-Thr(t-Bu)-Phe-Pro-OTmse 
• 108826-71-7 N-α-benzyloxycarbonyl-D-tryptophyl-N-ε-t-butoxycarbonyl-lysyl-O-t-butylthreonine 2-trimethylsilylethyl ester 
• 108827-20-9 Z-D-Trp-Lys(Boc)-Thr(t-Bu)-Phe-OMe 
• 111237-82-2 N^α-(benzyloxycarbonyl)-D-tryptophanyl-D-arginine methyl ester hydrochloride 

Relevant articles and documents

Beyond the Diketopiperazine Family with Alternatively Bridged Brevianamide F Analogues

A method for the preparation of 3,5-bridged piperazin-2-ones from a tryptophan-proline-based diketopiperazine is described using diphosgene to induce the ring closure. Density functional theory calculations were conducted to study the mechanism of this C-C bond formation. Several derivatives of the thus obtained α-chloroamine were synthesized by substitution of the chlorine atom using a range of O-, N-, S-, and C-nucleophiles. This novel class of brevianamide F analogues possess interesting breast cancer resistance protein inhibitory activity.

A concise preparation of the non-proteinogenic amino acid l-kynurenine

A concise and practical preparation of the non-proteinogenic amino acid l-kynurenine is reported. The synthetic approach is scalable and provides ready access to this valuable amino acid in either l- or d-stereochemistry starting from l- or d-tryptophan, respectively. In the optimized procedure, two discreet oxidation steps are applied sequentially to convert the tryptophan indole ring into the keto-aniline moiety contained within the kynurenine side chain.

Cyclodextrin-mediated deacylation of amino acid esters with marked stereoselectivity.

With respect to the hydrolysis (deacylation) of Z-D(L)-amino acid esters (N-(benzyloxycarbonyl)-D(L)-amino acid p-nitrophenyl esters) mediated by alpha-, beta- and gamma-cyclodextrins (CyDs), a remarkably high enantioselectivity (L/D=9.0) was observed for the deacylation of Ala substrate with gamma-CyD. The kinetic results on the basis of the Michaelis-Menten principle indicate that the enantioselectivity should be mainly originated in the deacylation process of substrates following the formation of gamma-CyD-substrate (1 : 1) complexes. The computer modeling (molecular mechanics) studies on the inclusion complexes are also described.