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

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

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

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

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.

Synergism between genome sequencing, tandem mass spectrometry and bio-inspired synthesis reveals insights into nocardioazine B biogenesis

Marine actinomycete-derived natural products continue to inspire chemical and biological investigations. Nocardioazines A and B (3 and 4), from Nocardiopsis sp. CMB-M0232, are structurally unique alkaloids featuring a 2,5-diketopiperazine (DKP) core functionalized with indole C3-prenyl as well as indole C3- and N-methyl groups. The logic of their assembly remains cryptic. Bioinformatics analyses of the Nocardiopsis sp. CMB-M0232 draft genome afforded the noz cluster, split across two regions of the genome, and encoding putative open reading frames with roles in nocardioazine biosynthesis, including cyclodipeptide synthase (CDPS), prenyltransferase, methyltransferase, and cytochrome P450 homologs. Heterologous expression of a twelve gene contig from the noz cluster in Streptomyces coelicolor resulted in accumulation of cyclo-l-Trp-l-Trp DKP (5). This experimentally connected the noz cluster to indole alkaloid natural product biosynthesis. Results from bioinformatics analyses of the noz pathway along with challenges in actinomycete genetics prompted us to use asymmetric synthesis and mass spectrometry to determine biosynthetic intermediates in the noz pathway. The structures of hypothesized biosynthetic intermediates 5 and 12-17 were firmly established through chemical synthesis. LC-MS and MS-MS comparison of these synthetic compounds with metabolites present in chemical extracts from Nocardiopsis sp. CMB-M0232 revealed which of these hypothesized intermediates were relevant in the nocardioazine biosynthetic pathway. This established the early and mid-stages of the biosynthetic pathway, demonstrating that Nocardiopsis performs indole C3-methylation prior to indole C3-normal prenylation and indole N1′-methylation in nocardioazine B assembly. These results highlight the utility of merging bioinformatics analyses, asymmetric synthetic approaches, and mass spectrometric metabolite profiling in probing natural product biosynthesis.

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.

A concise total synthesis of (+)-okaramine C

The first total synthesis of (+)-okaramine C is described. Our previously described selenocyclisation-oxidative deselenation sequence was used to establish a 3a-hydroxy-pyrrolo[2,3-b]-indole core, which was modified by selective epimerisation to the commo

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.

Direct Optical Resolution of Carboxylic Acids by Chyral HPLC on Tris(3,5-dimethylphenylcarbamate)s of Cellulose and Amylose

A variety of racemic carboxylic acids have been for the first time directly resolved by normal-phase, high-performance liquid chromatography using a hexane-2-propanol eluting system containing a small amount (ca. 1percent) of a strong carboxylic acid, like formic acid, trichloroacetic acid, and trifluoroacetic acid.

PAPAIN-ASSISTED RESOLUTION OF NATURAL AND XENOBIOTIC α-AMINO ACIDS

A new and convenient method for the preparation of pure enantiomers of α-amino acids is described.Industrial papain, catalyzes the synthesis of L-Z-amino acid ethyl esters in ethanolic medium, with good yields.These esters are obtained from DL-Z-amino acids with 100percent optical purity.Unreactive D-Z-amino acids are readily isolated from reaction medium.Physical constants of natural and xenobiotic L-Z-amino acid esters and D-Z-amino acids are described.

Origins of Micellar Diastereoselectivity

Thiol-functionalized surfactant micelles (n-C12H25N+Me2CH2CH2SH,Cl-) were used to cleave Z-Trp-Pro p-nitrophenyl dipeptide esters.Marked kinetic diastereoselectivity was observed in these reactions.For example at pH 8 and concentrations (ca.6-7)x1E-3 M, the micellar thiol cleaved the LL substrate 5-6 times more rapidly than its DL diastereomer.This kinetic diastereoselectivity was shown to develop at surfactant concentrations ca.5x1E-3 M, considerably above the cmc (ca.1x1E-3 M), i.e., at a second "critical concentration".Dynamic light-scattering measurements showed that micelles which had reacted with the LL (but not the DL) substrate underwent a marked increase in apparent hydrodynamic diameter (from ca. 15 to 26 nm) near this second critical concentration.Similar phenomena could be induced upon addition of 2x1E-5 M LL dipeptide surfactant reaction product to the thiol micelles.Micelles of n-C12H25N+Me2CH2CH2OH,Cl- or n-C12H25N+Me3,Cl- were unresponsive to such additions (light scattering).The results are discussed in terms of molecular and supramolecular interactions between surfactant and solubilizate molecules.

3-ACYL- AND 3-ALKOXYCARBONYL-2-OXAZOLONES AND THEIR HOMOPOLYMERS AS AMINO-PROTECTING REAGENTS

3-Acyl and 3-alkoxycarbonyl-2-oxazolones as well as their homopolymers serve as practically usefull N-protecting reagents of amines including α-amino acids.