22216-02-0

Basic information

• Product Name: Cyclo-(L)-Trp-(D)-Ala
• CAS NO: 22216-02-0
• Molecular Weight: 257.292
• Mol File: 22216-02-0.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: Cyclo-(L)-Trp-(D)-Ala(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclo-(L)-Trp-(D)-Ala(22216-02-0)
• EPA Substance Registry System: Cyclo-(L)-Trp-(D)-Ala(22216-02-0)

Safety Data

• Hazardous Substances Data: 22216-02-0(Hazardous Substances Data)

Upstream product

• 207349-24-4 Boc-Ala-Trp-OMe 
• 207349-41-5 Boc-D-Ala-D-Trp-OMe 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 
• 204980-52-9 D-alanyl-L-tryptophan methyl ester 
• 4299-70-1 L-tryptophan methyl ester 
• 91683-95-3 (3S)-cis-1-methyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester; hydrochloride 
• 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 
• 207349-25-5 (S)-2-((R)-2-tert-Butoxycarbonylamino-propionylamino)-3-(1H-indol-3-yl)-propionic acid methyl ester 
• 4299-70-1 D-Tryptophan methyl ester 
• 207349-42-6 (R)-2-((S)-2-tert-Butoxycarbonylamino-propionylamino)-3-(1H-indol-3-yl)-propionic acid methyl ester 
• 35661-39-3 N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine 
• 63430-66-0 N^α-(tert-butoxycarbonyl)-L-tryptophyl-L-alanine methyl ester 
• 73-22-3 L-Tryptophan 
• 7432-21-5 N-carbobenzyloxy-L-tryptophane 

Downstream Products

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

Relevant articles and documents

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

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.

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.