69876-37-5

Basic information

• Product Name: Z-TRP-OBZL
• Synonyms: N-ALPHA-CARBOBENZOXY-L-TRYPTOPHAN ALPHA-BENZYL ESTER;Z-L-TRYPTOPHAN BENZYL ESTER;Z-TRP-OBZL;Cbz-Trp-OBzl;N-α-Z-L-tryptophan benzyl ester;N-a-Z-L-tryptophanbenzylester;N-.ALPHA.-CBZ-L-TRYPTOPHAN BENZYL ESTER;N-Carbobenzyloxy-L-tryptphan benzyl ester
• CAS NO: 69876-37-5
• Molecular Formula: C₂₆H₂₄N₂O₄
• Molecular Weight: 428.48
• Product Categories: Tryptophan [Trp, W];Z-Amino Acids and Derivatives;Z-Amino acid series
• Mol File: 69876-37-5.mol

Chemical Properties

• Melting Point: 105-108℃
• Boiling Point: 656.7 °C at 760 mmHg
• Flash Point: 350.9 °C
• Appearance: White to off-white/Powder
• Density: 1.266 g/cm³
• Vapor Pressure: 4.04E-17mmHg at 25°C
• Refractive Index: 1.645
• Storage Temp.: Store at 0-5°C
• PKA: 10.93±0.46(Predicted)
• CAS DataBase Reference: Z-TRP-OBZL(CAS DataBase Reference)
• NIST Chemistry Reference: Z-TRP-OBZL(69876-37-5)
• EPA Substance Registry System: Z-TRP-OBZL(69876-37-5)

Safety Data

• Hazardous Substances Data: 69876-37-5(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white powder

InChI:InChI=1/C26H24N2O4/c29-25(31-17-19-9-3-1-4-10-19)24(15-21-16-27-23-14-8-7-13-22(21)23)28-26(30)32-18-20-11-5-2-6-12-20/h1-14,16,24,27H,15,17-18H2,(H,28,30)/t24-/m0/s1

Upstream product

• 100-51-6 benzyl alcohol 
• 7432-21-5 N-carbobenzyloxy-L-tryptophane 
• 73-22-3 L-Tryptophan 
• 501-53-1 benzyl chloroformate 
• 67413-25-6 benzyl (-)-(2S)-1-trityl-aziridine-2-carboxylate 
• 4299-69-8 L-tryptophane benzyl ester 
• 120-72-9 indole 
• 83824-80-0 benzyl (2S)-1-benzyloxycarbonyl-aziridine-2-carboxylate 

Downstream Products

• 118869-29-7 Z-Trp(PO₃Me₂)-OBzl 
• 7432-21-5 N-carbobenzyloxy-L-tryptophane 
• 602330-18-7 (2S)-2-amino-3-[1-(4-methylbenzoyl)indol-3-yl]propanoic acid 
• 16709-25-4 (S)-α-methyltryptophan 
• 200716-93-4 (2S,3aR,8aS)-2,3,3a,8a-Tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid tribenzyl ester 
• 200716-94-5 (2S,3aR,8aR)-2-Methyl-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid tribenzyl ester 
• 1094607-28-9 dibenzyl (2S)-3,3a,8,8a-tetrahydropyrrolo[2,3-b]indol-1,2 (2H)-dicarboxylate 
• 1224881-40-6 benzyl (S)-1-(benzyloxycarbonyl)-2-(1-phenyl-1H-indol-3-yl)ethylcarbamate 
• 1224881-41-7 benzyl (S)-1-(benzyloxycarbonyl)-2-(1-(naphthalen-yl)-1H-indol-3-yl)ethylcarbamate 
• 1224881-42-8 benzyl (S)-1-(benzyloxycarbonyl)-2-(1-(4'-phenylphenyl)-1H-indol-3-yl)ethylcarbamate 
• 1335304-38-5 C₃₇H₄₂N₄O₈ 

Relevant articles and documents

Scandium-mediated opening of aziridine carboxylates: A facile synthesis of aryl substituted tryptophans

The treatment of enantiomerically pure L-serine-derived N-Cbz- or N-Fmoc-aziridine carboxylates with indole derivatives in the presence of a stoichiometric amount of Sc(OTf)3 in dichloromethane at 0°C or RT gives the aryl-substituted and protected tryptop

Synthesis and evaluation of oxindoles as promising inhibitors of the immunosuppressive enzyme indoleamine 2,3-dioxygenase 1

Indoleamine 2,3-dioxygenase 1 (IDO1) is considered as an important therapeutic target for the treatment of cancer, chronic infections and other diseases that are associated with immune suppression. Recent developments in understanding the catalytic mechanism of the IDO1 enzyme revealed that conversion of l-tryptophan (l-Trp) to N-formylkynurenine proceeded through an epoxide intermediate state. Accordingly, we synthesized a series of 3-substituted oxindoles from l-Trp, tryptamine and isatin. Compounds with C3-substituted oxindole moieties showed moderate inhibitory activity against the purified human IDO1 enzyme. Their optimization led to the identification of potent compounds, 6, 22, 23 and 25 (IC50 = 0.19 to 0.62 μM), which are competitive inhibitors of IDO1 with respect to l-Trp. These potent compounds also showed IDO1 inhibition potencies in the low-micromolar range (IC50 = 0.33-0.49 μM) in MDA-MB-231 cells. The cytotoxicity of these potent compounds was trivial in different model cancer (MDA-MB-231, A549 and HeLa) cells and macrophage (J774A.1) cells. Stronger selectivity for the IDO1 enzyme (124 to 210-fold) over the tryptophan 2,3-dioxygenase (TDO) enzyme was also observed for these compounds. These results suggest that the oxindole moiety of the compounds could mimic the epoxide intermediate state of l-Trp. Therefore, the structural simplicity and low-micromolar inhibition potencies of these 3-substituted oxindoles make them quite attractive for further investigation of IDO1 function and immunotherapeutic applications.

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.

Chemzymes: A new class of structurally rigid tricyclic amphibian organocatalyst inspired by natural product

"Chemical Equation Presented" A new class of structurally rigid tricyclic amphibian chiral catalyst was rationally designed based on the hexahydropyrrolo[2,3-b]indole skeleton as a new type of chemzyme. This new type of chemzyme possesses a structurally rigid tricyclic skeleton and a chiral pocket which provides a well-organized chiral environment for asymmetric induction, as well as a hydrophobic pocket to enable organocatalytic reactions to proceed smoothly both in organic solvents and in water.

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

CONSTRUCTION OF OPTICALLY PURE TRYPTOPHANS FROM SERINE DERIVED AZIRIDINE-2-CARBOXYLATES

The possibility of preparing optically pure tryptophan derivatives from various substituted indoles and (2R)- or (2S)-2-aziridinecarboxylates has been examined.Zinc triflate was found to be the only Lewis acid capable of bringing about this reaction in mo

Synthesis of N(1)-Phosphorylated Tryptophan Derivatives

The first synthesis of the N(1)-(dimethylphosphono)tryptophan derivatives Z-Trp(PO3Me2)-OBzl and Boc-Trp(PO3Me2)-ONBzl by reaction of the lithium indolate of protected tryptophan derivatives Z-Trp-OBzl and Boc-Trp-ONBzl with dimethyl phosphorochloridate is described.The N(1)-(dimethylphosphono)tryptophan or Trp(Dmop) derivatives are stable to hydrogenation, and to TFA and high HF treatment, and can be fully deprotected with TFMSA/TFA/m-cresol/dimethyl sulfide or TFMSA/TFA/m-cresol/thioanisole to yield the novel hydrophilic amino acid N(1)-phosphonotryptophan quantitatively.Weak base treatment of Trp(Dmop) compounds yields N(1)-(methylphosphono)tryptophan derivatives.

Synyhesis of N(1)-Phosphotryptophan

N(1)-Phospho-L-tryptophan was prepared by phosphorylation with dimethyl phosphorochloridate of benzyl Nα-(benzyloxycarbonyl)-N(1)-lithiotryptophanate followed by deprotection with CF3SO3H-CF3CO2H-Me2S-m-cresol.