82597-82-8

Basic information

• Product Name: CYCLO(-PHE-TRP)
• Synonyms: CYCLO(-PHE-TRP);3-(1H-Indol-3-ylmethyl)-6-(phenylmethyl)-2,5-piperazinedione;Rugulosuvine;Cyclo(-L-Phe-L-Trp)≥ 99% (HPLC)
• CAS NO: 82597-82-8
• Molecular Formula: C₂₀H₁₉N₃O₂
• Molecular Weight: 333.38
• Mol File: 82597-82-8.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 705.5°C at 760 mmHg
• Flash Point: 380.5°C
• Appearance: /
• Density: 1.279g/cm³
• Vapor Pressure: 9.47E-20mmHg at 25°C
• Refractive Index: 1.658
• Storage Temp.: Store at 0°C
• PKA: 13.17±0.60(Predicted)
• CAS DataBase Reference: CYCLO(-PHE-TRP)(CAS DataBase Reference)
• NIST Chemistry Reference: CYCLO(-PHE-TRP)(82597-82-8)
• EPA Substance Registry System: CYCLO(-PHE-TRP)(82597-82-8)

Safety Data

• Hazardous Substances Data: 82597-82-8(Hazardous Substances Data)

Usage

Chemical Properties

White solid

InChI:InChI=1/C20H19N3O2/c24-19-17(10-13-6-2-1-3-7-13)22-20(25)18(23-19)11-14-12-21-16-9-5-4-8-15(14)16/h1-9,12,17-18,21H,10-11H2,(H,22,25)(H,23,24)

Upstream product

• 144599-95-1 N^α-(tert-butoxycarbonyl)-1-methyl-L-tryptophan 
• 918902-48-4 Boc-Trp(Boc)-Phe-OMe 
• 35661-40-6 N-Fmoc L-Phe 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 
• 108787-56-0 L-phenylalanyl-L-tryptophan methyl ester 
• 7432-21-5 N-carbobenzyloxy-L-tryptophane 
• 6683-28-9 methyl ((benzyloxy)carbonyl)-L-tryptophyl-L-phenylalaninate 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 4299-70-1 L-tryptophan methyl ester 
• 83522-39-8 N^α-(tert-butoxycarbonyl)-L-phenylalanyl-L-tryptophan methyl ester 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 76327-08-7 L-phenylalaninyl-L-triptophane methyl ester hydrochloride 
• 198632-67-6 (S)-2-[(S)-2-Amino-3-(1H-indol-3-yl)-propionylamino]-3-phenyl-propionic acid methyl ester 
• 13139-14-5 Boc-Trp-OH 

Downstream Products

• 1221435-63-7 C₂₅H₂₇N₃O₂ 
• 1221185-87-0 C₂₇H₂₉N₃O₃ 
• 1194053-19-4 C₂₅H₂₇N₃O₂ 
• 1429318-50-2 C₂₆H₂₃N₃O₂ 
• 1429318-53-5 C₂₆H₂₃N₃O₂ 
• 1429318-66-0 C₂₇H₂₅N₃O₂ 
• 1429318-64-8 C₂₇H₂₅N₃O₂ 
• 1429318-68-2 C₂₈H₂₇N₃O₂ 
• 1429318-70-6 C₂₇H₂₅N₃O₃ 
• 1429318-71-7 C₃₀H₂₅N₃O₂ 
• 1429318-72-8 C₂₆H₂₂BrN₃O₂ 

Relevant articles and documents

Oxidative couplings on tryptophan-based diketopiperazines leading to fused and bridged chemotypes

New chemotypes are obtained from tryptophan-containing diketopiperazines through selective C-C or C-N intramolecular oxidative couplings. The choice of the oxidant source dictates the outcome of the reaction.

A Mutasynthesis Approach with a Penicillium chrysogenum ΔroqA Strain Yields New Roquefortine D Analogues

Penicillium chrysogenum, which lacks the roqA gene, processes synthetic, exogenously added histidyltryptophanyldiketopiperazine (HTD) to yield a set of roquefortine-based secondary metabolites also produced by the wild-type strain. Feeding a number of synthetic HTD analogues to the ΔroqA strain gives rise to the biosynthesis of a number of new roquefortine D derivatives, depending on the nature of the synthetic HTD added. Besides delivering semisynthetic roquefortine analogues, the mutasynthesis studies presented here also shed light on the substrate preferences and molecular mechanisms employed by the roquefortine C/D biosynthesis gene cluster, knowledge that may be tapped for the future development of more complex semisynthetic roquefortine-based secondary metabolites.

Efficient synthesis of 2,5-diketopiperazines using microwave assisted heating

In this study a general, efficient and environmentally benign solution phase synthesis of 2,5-diketopiperazines (DKPs) using microwave assisted heating in water is described. A series of 11 structurally different DKPs have been synthesized from dipeptide methyl esters. A range of common laboratory solvents have been tested as well as different reaction times and temperatures. Both classic thermal and microwave assisted heating have been investigated. Microwave assisted heating for 10 min using water as solvent proved, by far, to be the most efficient method of cyclization giving moderate to excellent yields (63-97%) of DKPs. In contrast to other published procedures, this method seems independent of the amino acid sequence.