22839-22-1

Basic information

• Product Name: Cyclo(D-Ala-L-Trp-)
• Synonyms: (3S,6R)-3-(1H-Indol-3-ylmethyl)-6-methyl-2,5-piperazinedione;Cyclo(D-Ala-L-Trp-)
• CAS NO: 22839-22-1
• Molecular Weight: 0
• Mol File: 22839-22-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Cyclo(D-Ala-L-Trp-)(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclo(D-Ala-L-Trp-)(22839-22-1)
• EPA Substance Registry System: Cyclo(D-Ala-L-Trp-)(22839-22-1)

Safety Data

• Hazardous Substances Data: 22839-22-1(Hazardous Substances Data)

Upstream product

• 28944-98-1 Z-L-Ala-L-Trp-OMe 
• 207349-24-4 Boc-Ala-Trp-OMe 
• 300766-86-3 (3S,6S)-6-(3'-indolylmethyl)-3-methyl-1-(2,4-dimethoxybenzyl)-2,5-piperazinedione 
• 4299-70-1 L-tryptophan methyl ester 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 
• 7432-21-5 N-carbobenzyloxy-L-tryptophane 
• 73-22-3 L-Tryptophan 
• 63430-66-0 N^α-(tert-butoxycarbonyl)-L-tryptophyl-L-alanine methyl ester 
• 35661-39-3 N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine 
• 207349-41-5 Boc-D-Ala-D-Trp-OMe 
• 204980-54-1 (1S,3S)-2-((R)-2-tert-Butoxycarbonylamino-propionyl)-1-methyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester 
• 91683-95-3 (3S)-cis-1-methyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester; hydrochloride 
• 204980-52-9 D-alanyl-L-tryptophan methyl ester 
• 207349-25-5 (S)-2-((R)-2-tert-Butoxycarbonylamino-propionylamino)-3-(1H-indol-3-yl)-propionic acid methyl ester 

Downstream Products

• 1429318-81-9 C₂₂H₁₈BrF₃N₄O₃ 
• 1429318-54-6 C₂₀H₁₉N₃O₂ 
• 1859-87-6 Echinulin 
• 1429318-56-8 C₂₀H₁₉N₃O₂ 
• 374114-89-3 (3R,6S)-1-(o-Azidobenzoyl)-3-(3-indolylmethyl)-6-methyl-2,5-piperazinedione 
• 374114-86-0 (3S,6R)-1-(o-Azidobenzoyl)-3-methyl-6-(3-indolylmethyl)-2,5-piperazinedione 

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.

Conditional changes enhanced production of bioactive metabolites of marine derived fungus Eurotium rubrum

Metabolites of marine derived fungus Eurotium rubrum MPUC136 differed between cultivation on wheat medium and Czapek-Dox agar medium. Melanin synthesis inhibitory activity of crude extract of culture on wheat medium showed stronger activity than that of crude extract of culture on Czapek-Dox agar medium. A new diketopiperazine compound isoechinulin D (1) and eight reported diketopiperazines (2–9) were isolated from the crude extract of wheat medium. The structure of 1 was established using NMR, MS and IR methods. 2–5 inhibited melanogenesis using B16 melanoma cells (IC50?=?68, 2.4, 83, 9.1?μM each). Structure–Activity-Relationships of diketopiperazines (1–10) indicated the importance of the prenyl groups at C-2, C-5 and C-7, the vinyl group at C-12 to C-25 and the sp2carbons at C-8 and C-9. Isolated compounds (1–9) were not or slightly observed from the extracts of Czapek-Dox agar medium by HPLC analysis, suggesting that different cultivation processes could affect metabolism and enhance bioactivities.

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.

Prenylation at the indole ring leads to a significant increase of cytotoxicity of tryptophan-containing cyclic dipeptides

Fourteen tryptophan-containing cyclic dipeptides 1a-14a, including all four stereoisomers of cyclo-Trp-Pro and cyclo-Trp-Ala, were converted to their C2-regularly prenylated derivatives 1b-14b in the presence of dimethylallyl diphosphate by using the purified recombinant FtmPT1 as catalyst. The enzyme products were isolated on HPLC in preparative scales and their structures were elucidated by NMR and MS analyses. The cytotoxic effects of the prenylated products and their substrates were tested with human leukemia K562 and ovarian cancer A2780 sens and A2780 CisR cell lines. Preliminary results have been clearly shown that prenylation at C2 led to a significant increase of the cytotoxicity of the tested cyclic dipeptides in all the 14 cases. The second amino acid and the stereochemistry of tryptophan moiety of the cyclic dipeptides showed less influence on the cytotoxicity of the tested compounds.

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

Regioselective N-acylation of 3-arylmethylpiperazine-2,5-diones: Short synthesis of (-)-glyantrypine and (-)-fumiquinazoline F

The folded conformation of the 3-arylmethyl substituent in 2,5-bis-O-trimethylsilyl-3,6-dihydropyrazines derived from the corresponding piperazine-2,5-diones, shields the N(1)-position allowing monoacylation at the neighbouring nitrogen atom. This regioselectivity was used to develop a four-step total synthesis of (-)-glyantrypine and (-)-fumiquinazoline F starting from D-tryptophan methyl ester.

Synthesis of a seco analogue of ardeemin

(1S,4S)-1-Indolylmethyl-4-methyl-2,4-dihydro-1H-pyrazino[2,1-b]-q uinazaline-3,6-dione, a seco analogue of ardeemin, was synthesized in six steps from L-tryptophan methyl ester via an N-protected 2,5-piperazinedione and using an aza-Wittig reaction for the preparation of the quinazoline system. The final acid-promoted deprotection required tuning of the reaction conditions in order to minimize a side reaction involving loss of the indolylmethyl side chain.

Stereochemical issues related to the synthesis and reactivity of pyrazino [2',1'-5,1] pyrrolo[2,3-b]indole- 1,4-diones

The cyclization of all four diastereoisomers of cyclo-(Trp-Ala) to the corresponding 3,5a,6,10b,11,11a-hexahydro-2H-pyrazino[2',1'-5,1]pyrrolo[2,3- b]indoles is studied from the stereochemical point of view. Epimerization of the tryptophan stereocenter du

Conformational effects in reversed-phase liquid chromatographic separation of diastereomers of cyclic dipeptides

The capacity factors, k′, of 11 cyclic dipeptides (X-Y) including diastereomers have been determined on an RP-HPLC column in 30% and 50% methanol and 10%, 30%, and 50% acetonitrile solutions. These factors are roughly correlated with hydrophobic parameters, such as octanol-water partition coefficients estimated and k′ values for alcohols. For a pair of diastereomers of cyclic (L-X-L-Phe) and (L-X-D-Phe) derivatives k′LL is larger than k′LD and for cyclic (D-Ala-L-Trp) and (L-Ala-L-Trp) k′LL is smaller than k′DL, particularly in highly aqueous solutions. These elution orders can be well predicted by the holistic molecular surface area approach which takes into account the folded structures of cyclic dipeptides. The present results will be useful for prediction of the log k′ values of larger peptides and the hydrophobicity and related properties of peptides.