6521-48-8

Upstream product

• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 13139-14-5 Boc-Trp-OH 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 144599-95-1 N^α-(tert-butoxycarbonyl)-1-methyl-L-tryptophan 
• 918902-48-4 Boc-Trp(Boc)-Phe-OMe 
• 108787-56-0 L-phenylalanyl-L-tryptophan methyl ester 
• 35661-40-6 N-Fmoc L-Phe 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 
• 7432-21-5 N-carbobenzyloxy-L-tryptophane 
• 6683-28-9 methyl ((benzyloxy)carbonyl)-L-tryptophyl-L-phenylalaninate 
• 4299-70-1 L-tryptophan methyl ester 
• 83522-39-8 N^α-(tert-butoxycarbonyl)-L-phenylalanyl-L-tryptophan methyl ester 
• 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 

Downstream Products

• 108508-09-4 (3S,5aR,10bS,11aS)-3-Benzyl-10b-hydroxy-2,3,6,10b,11,11a-hexahydro-5aH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione 
• 108431-24-9 (3S,5aS,10bR,11aS)-3-Benzyl-10b-hydroxy-2,3,6,10b,11,11a-hexahydro-5aH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione 
• 403655-36-7 (3S,6S)-3-Benzyl-6-(2,3-dihydro-1H-indol-3-ylmethyl)-piperazine-2,5-dione 
• 180910-59-2 (3S,6S)-(-)-6-(1-hydroxyindol-3-ylmethyl)-3-benzyl-2,5-piperazinedione 
• 403655-43-6 Benzoic acid 3-((2S,5S)-5-benzyl-3,6-dioxo-piperazin-2-ylmethyl)-indol-1-yl ester 
• 1221435-63-7 C₂₅H₂₇N₃O₂ 
• 1221185-87-0 C₂₇H₂₉N₃O₃ 
• 263759-12-2 deAc-fructigenine A 
• 1233078-22-2 diethyl 2-(3-(((2S,5S)-5-benzyl-3,6-dioxopiperazin-2-yl)methyl)-1H-indol-2-yl)malonate 
• 1194053-19-4 C₂₅H₂₇N₃O₂ 
• 1429318-50-2 C₂₆H₂₃N₃O₂ 
• 1429318-53-5 C₂₆H₂₃N₃O₂ 
• 1429318-66-0 C₂₇H₂₅N₃O₂ 
• 1429318-64-8 C₂₇H₂₅N₃O₂ 

Relevant academic research and scientific papers

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.

Synthesis and Biological Evaluations of a Series of Thaxtomin Analogues

Thaxtomins are a unique family of phytotoxins with unique 4-nitroindole and diketopiperazine fragments possessing potential herbicidal activities. This work presents the total synthesis of natural product thaxtomin C and its analogues. The extensive struc

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.

Copper-catalyzed diastereoselective arylation of tryptophan derivatives: Total synthesis of (+)-naseseazines A and B

A copper-catalyzed arylation of tryptophan derivatives is reported. The reaction proceeds with high site-and diastereoselectivity to provide aryl pyrroloindoline products in one step from simple starting materials. The utility of this transformation is highlighted in the five-step syntheses of the natural products (+)-naseseazine A and B.

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.

A facile pathway to synthesize diketopiperazine derivatives

Eighteen diketopiperazines (DKPs) were synthesized in good yields by a solid-phase protocol. This synthesis reveals that the OPac linker between the peptidyl and resin support is favorable to DKP-ring formation and offers a facile and effective way to prepare diverse DKP libraries for combinatorial chemistry.

Simple synthesis of 1,3,4,5a,6,10b,11,11a-octahydro-2H-pyrazino[1′,2′:1,5]pyrrolo[2, 3-b]indole derivatives based on 1-hydroxyindole chemistry

3-Substituted (3S,6S)-6-(1-hydroxyindol-3-ylmethyl)-2,5-piperazinediones are prepared for the first time. They are shown to be suitable intermediates for the synthesis of 3,10b-disubstituted (3S,5aR,10bS,11as)-1,3,4,5a,6,10b,11, 11a-octahydro-2H-pyrazino[