99095-60-0

Upstream product

• 2666-93-5 (S)-Leu-OMe 
• 13139-15-6 N-tert-butoxycarbonyl-L-leucine 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 
• 141595-69-9 N-t-butyloxycarbonyl-L-leucyl-L-tryptophan methyl ester 
• 35661-60-0 Fmoc-Leu-OH 
• 13139-14-5 Boc-Trp-OH 
• 7432-21-5 N-carbobenzyloxy-L-tryptophane 
• 2419-36-5 Cbz-Trp-Leu-OMe 
• 128719-24-4 N-tert-butoxycarbonyl-L-tryptophan-L-leucine methylester 

Downstream Products

• 1221185-82-5 C₂₂H₂₉N₃O₂ 
• 215121-47-4 (2S,10aS,5aS,4aS)-5a-(1,1-dimethylprop-2-enyl)-2-(2-methylpropyl)-1,2,3,4,4a,5,5a,10a-octahydro-10H-pyrazino[1',2':1,2]pyrrolo[4,5-b]indole-1,4-dione 
• 403655-45-8 (3S,6S)-(-)-6-(1-benzoyloxyindol-3-ylmethyl)-3-isobutyl-2,5-piperazinedione 

Relevant academic research and scientific papers

Three types of induced tryptophan optical activity compared in model dipeptides: Theory and experiment

The tryptophan (Trp) aromatic residue in chiral matrices often exhibits a large optical activity and thus provides valuable structural information. However, it can also obscure spectral contributions from other peptide parts. To better understand the indu

A [3,3] sigmatropic and novel ipso [3,3] sigmatropic rearrangement of 1-hydroxyindole chemistry

Utilizing 1-aryloxyindole derivatives, we found a new type of [3,3] sigmatropic rearrangement reaction. We named it as ipso [3,3] sigmatropic rearrangement. The product structures are strictly determined by X-ray crystallographic analysis. Normal [3,3] sigmatropic rearrangement of 1-hydroxyindole derivative was found to be a useful synthetic method for 2H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione derivative.

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.

Mimicking the Main Events of the Biosynthesis of Drimentines: Synthesis of Δ8′-Isodrimentine A and Related Compounds

Drimentines are a family of tetracyclic alkaloids biosynthetically originating from the condensation of sesquiterpene units onto cyclic dipeptides. A straightforward assembly of the fused “pyrroloindoline–diketopiperazine” core of drimentines is described herein and used for the synthesis of Δ8′-isodrimentine A. The strategy involves a bio-inspired indole dearomatization of a tryptophan-containing cyclodipeptide by a drimane-type decaline followed by the intramolecular trapping of the resulting indolenine intermediate in an uninterrupted reactive sequence. The starting diketopiperazine was prepared by classical peptidic coupling and the drimane-type decaline from (+)-sclareolide. A fully biomimetic approach with a linear sesquiterpene unit is also reported and led to farnesylated pyrroloindoline–diketopiperazines, which correspond to the proposed biosynthetic precursors of both drimentines A and D. The end product Δ8′-isodrimentine A and its congeners were evaluated in vitro for their cytotoxic activities against three human tumor cell lines.

Cyclic dipeptides exhibit potency for scavenging radicals

Twenty kinds of cyclic dipeptides containing l-leucine were synthesized, and their antioxidant activity against .OH and O2·- was investigated. Compounds possessing polar amino acid residues, such as Asp, Cys, Glu, Lys, Pro, Ser, and Trp, exhibited higher antioxidant activity against .OH than vitamin E. However, only cyclo(l-Cys-l-Leu) scavenged O2·-.

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[