38136-70-8

Basic information

• Product Name: Cyclo(L-Pro-L-Trp-)
• Synonyms: (3S)-2,3,6,7,8,8aα-Hexahydro-3β-(1H-indol-3-ylmethyl)pyrrolo[1,2-a]pyrazine-1,4-dione;(3S,8aα)-3β-(1H-Indole-3-ylmethyl)octahydropyrrolo[1,2-a]pyrazine-1,4-dione;Brevianamide F;Cyclo(L-Pro-L-Trp-);Cyclo(L-Trp-L-Pro-)
• CAS NO: 38136-70-8
• Molecular Formula: C₁₆H₁₇N₃O₂
• Molecular Weight: 283.32508
• Mol File: 38136-70-8.mol
• Article Data: 18

Chemical Properties

• Melting Point: 165-167 °C
• Boiling Point: 633.2°C at 760 mmHg
• Flash Point: 336.8°C
• Appearance: /
• Density: 1.37g/cm³
• Vapor Pressure: 6.11E-16mmHg at 25°C
• Refractive Index: 1.689
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 13.20±0.40(Predicted)
• CAS DataBase Reference: Cyclo(L-Pro-L-Trp-)(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclo(L-Pro-L-Trp-)(38136-70-8)
• EPA Substance Registry System: Cyclo(L-Pro-L-Trp-)(38136-70-8)

Safety Data

• Hazardous Substances Data: 38136-70-8(Hazardous Substances Data)

Usage

Description

Cyclo(L-Pro-L-Trp-), also known as Brevianamide F, is a pyrrolopyrazine compound that is a hexahydropyrrolo[1,2-a]pyrazine-1,4-dione bearing an indol-3-ylmethyl substituent at position 3. It is the 3S,8aS-diastereomer, obtained by formal cyclocondensation of L-tryptophan and L-proline. Cyclo(L-Pro-L-Trp-) is an alkaloid metabolite produced by various Streptomyces, Actinomycetes, and Aspergillus strains and has diverse biological activities.

Uses

1. Used in Pharmaceutical Industry:
Cyclo(L-Pro-L-Trp-) is used as a bioactive natural product for the preparation, reactions, and medicinal and chemical properties of diketopiperazines. It acts as a reagent in the total synthesis and antitumor activity in vitro of glioperazine C and its derivatives, as well as in the synthesis and biological evaluation of a post-synthetically Trp-based diketopiperazine and its antitumor structure-activity relationship.
2. Used in Antimicrobial Applications:
Cyclo(L-Pro-L-Trp-) is used as an antimicrobial agent, inhibiting the growth of M. luteus and S. aureus in an inhibitory disc assay when used at a concentration of 30 μg/disc. It also shows activity against the Bacille Calmette-Guerin M. bovis strain with a minimum inhibitory concentration (MIC) of 12.5 μg/ml.
3. Used in Antifouling Applications:
In the marine industry, Cyclo(L-Pro-L-Trp-) is used as an antifouling agent, inhibiting the attachment of B. neritina larvae to PVC plates without inducing lethality. It has an effective concentration (EC50) of 6.35 μg/ml and a lethal concentration (LC50) of greater than 200 μg/ml in paint used to coat PVC plates.

InChI:InChI=1/C16H17N3O2/c20-15-14-6-3-7-19(14)16(21)13(18-15)8-10-9-17-12-5-2-1-4-11(10)12/h1-2,4-5,9,13-14,17H,3,6-8H2,(H,18,20)/t13-,14-/m0/s1

Upstream product

• 2133-40-6 D-proline methyl ester hydrochloride 
• 7432-21-5 N-carbobenzyloxy-L-tryptophane 
• 236123-12-9 N-(t-Boc)-L-Trp-L-ProNH₂ 
• 13139-14-5 Boc-Trp-OH 
• 813452-60-7 Fmoc-(S)-Trp-OAllyl 
• 2133-40-6 L-proline methyl ester monohydrochloride 
• 1343483-76-0 1-{6-[4-(N-benzylcarbamoyl)benzyloxymethyl]tetrahydropyran-2-yl}-N-(9-fluorenylmethoxycarbonyl)-(S)-tryptophan allyl ester 
• 55782-87-1 N-carbobenzyloxy-L-tryptophanyl-L-proline methyl ester 
• 92178-03-5 L-tryptophan allyl ester 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 
• 1228076-72-9 N-Fmoc-L-Pro-L-Trp-OMe 
• 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

• 34610-68-9 deoxybrevianamide E 
• 1429318-79-5 C₂₄H₂₀BrF₃N₄O₃ 
• 1429318-80-8 C₂₂H₂₁BrN₄O₂ 
• 1429318-62-6 C₂₂H₂₁N₃O₂ 
• 1454306-26-3 (3S,8aS)-3-((2-(p-tolyl)-1H-indol-3-yl)methyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 
• 1454306-27-4 (3S,8aS)-3-((2-(4-methoxyphenyl)-1H-indol-3-yl)methyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 
• 1454306-28-5 (3S,8aS)-3-((2-(4-(trifluoromethyl)phenyl)-1H-indol-3-yl)methyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 
• 1454306-29-6 (3S,8aS)-3-((2-(4-chlorophenyl)-1H-indol-3-yl)methyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 
• 1454306-30-9 methyl 4-(3-(((3S,8aS)-1,4-dioxooctahydropyrrolo[1,2-a]pyrazin-3-yl)methyl)-1H-indol-2-yl)benzoate 
• 1454306-31-0 (3S,8aS)-3-((2-(2-methoxyphenyl)-1H-indol-3-yl)methyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 
• 1454306-32-1 (3S,8aS)-3-((2-(2-(trifluoromethyl)phenyl)-1H-indol-3-yl)methyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 
• 1454306-33-2 (3S,8aS)-3-((2-(2-chlorophenyl)-1H-indol-3-yl)methyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 
• 1454306-34-3 (3S,8aS)-3-((2-(3-methoxyphenyl)-1H-indol-3-yl)methyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 
• 1454306-35-4 (3S,8aS)-3-((2-(3-(trifluoromethyl)phenyl)-1H-indol-3-yl)methyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 

Relevant articles and documents

Synthesis and evaluation of microtubule assembly inhibition and cytotoxicity of prenylated derivatives of cyclo-L-Trp-L-Pro

The synthesis of three isoprenylated derivatives of cyclo-L-Trp-L-Pro is described. These substances have been evaluated for cytotoxic activity in rat normal fibroblast 3Y1 cells and have also been evaluated in vitro for the inhibition of microtubule assembly. Copyright (C) 2000 Elsevier Science Ltd.

A concise synthesis of (-)-dihydrospirotryprostatin B via tandem Michael addition

The asymmetric synthesis of (-)-dihydrospirotryprostatin B (3), a cytostatic spiro[pyrrolidine-3,3′-oxindole] alkaloid, has been accomplished in 8 longest linear steps (LLS) from commercially available amino acids. The key step of the synthetic approach consists of the tandem Michael addition of oxindole derived from dipeptide diketopiperazine to alkynone, leading to the rapid construction of the spiro[pyrrolidine-3,3′-oxindole] scaffold with the consecutive quaternary spiro carbon center and chiral tertiary amine being diastereoselectively established.

Beyond the Diketopiperazine Family with Alternatively Bridged Brevianamide F Analogues

A method for the preparation of 3,5-bridged piperazin-2-ones from a tryptophan-proline-based diketopiperazine is described using diphosgene to induce the ring closure. Density functional theory calculations were conducted to study the mechanism of this C-C bond formation. Several derivatives of the thus obtained α-chloroamine were synthesized by substitution of the chlorine atom using a range of O-, N-, S-, and C-nucleophiles. This novel class of brevianamide F analogues possess interesting breast cancer resistance protein inhibitory activity.

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.