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cyclo(L-leucyl-L-tryptophyl)

CAS No.
15136-34-2
Chemical Name:
cyclo(L-leucyl-L-tryptophyl)
Synonyms
c(Leu-Trp);Cyclo(Trp-Leu);cyclo-L-Trp-L-Leu;Cyclo(L-Leu-L-Trp);cyclo(L-leucyl-L-tryptophyl);(3S,6S)-3-(1H-indol-3-ylmethyl)-6-(2-methylpropyl)piperazine-2,5-dione;2,5-Piperazinedione, 3-(1H-indol-3-ylmethyl)-6-(2-methylpropyl)-, (3S,6S)-
CBNumber:
CB11307048
Molecular Formula:
C17H21N3O2
Molecular Weight:
299.37
MDL Number:
MOL File:
15136-34-2.mol
MSDS File:
SDS
Last updated:2025-04-17 18:22:24
Product description Number Pack Size Price
Cyclo(L-Leu-L-Trp) ≥95% 24942 5mg $267
Cyclo(L-Leu-L-Trp) ≥95% 24942 25mg $931
Cyclo(-Leu-Trp) FC108311 10mg $229.7
Cyclo(-Leu-Trp) FC108311 25mg $430.75
Cyclo(-Leu-Trp) FC108311 50mg $670

cyclo(L-leucyl-L-tryptophyl) Properties

Boiling point 635.2±45.0 °C(Predicted)
Density 1.182±0.06 g/cm3(Predicted)
storage temp. Store at -20°C
solubility Methanol: Soluble
form A solid
pka 13.21±0.60(Predicted)

cyclo(L-leucyl-L-tryptophyl) price More Price(18)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Cayman Chemical 24942 Cyclo(L-Leu-L-Trp) ≥95% 15136-34-2 5mg $267 2026-04-30 Buy
Cayman Chemical 24942 Cyclo(L-Leu-L-Trp) ≥95% 15136-34-2 25mg $931 2026-04-30 Buy
Biosynth FC108311 Cyclo(-Leu-Trp) 15136-34-2 10mg $229.7 2026-06-04 Buy
Biosynth FC108311 Cyclo(-Leu-Trp) 15136-34-2 25mg $430.75 2026-06-04 Buy
Biosynth FC108311 Cyclo(-Leu-Trp) 15136-34-2 50mg $670 2026-06-04 Buy
Product number Packaging Price Buy
24942 5mg $267 Buy
24942 25mg $931 Buy
FC108311 10mg $229.7 Buy
FC108311 25mg $430.75 Buy
FC108311 50mg $670 Buy

cyclo(L-leucyl-L-tryptophyl) Chemical Properties,Uses,Production

Description

Cyclo(L-Leu-L-Trp) is a diketopiperazine metabolite originally isolated from Penicillium.1 It is active against various bacteria (MICs = 125-1000 μg/ml) and fungi (MICs = 8-64 μg/ml), and it inhibits the production rate of hydroxy radicals in an electron spin resonance (ESR) spectroscopy-based assay (IC50 = 1.8 μM).2,3 Cyclo(L-Leu-L-Trp) is a bitter tastant that can rapidly permeate rat taste cell membranes ex vivo when used at a concentration of 1 mM.4 It also acts as a melatonin receptor agonist in X. laevis melanophores, inhibiting cAMP accumulation when used at a concentration of 20 μM, an effect that is blocked by the melatonin receptor antagonist luzindole .5

Uses

Cyclo(L-leucyl-L-tryptophyl) (Cyclo(-Leu-Trp)) is a cyclic dipeptide that inhibits a various of bacteria and fungi. Cyclo(L-leucyl-L-tryptophyl) is a melatonin receptor agonist and is also used as a bitter ligand[1][2][3].

References

1. Solov'eva, T.F., Baskunov, B.P., Nefedova, M.Y., et al. Biosynthesis of leucyl-tryptophanyl-diketopiperazine by a culture of Penicillium aurantio-virens and the characteristics of its production Mikrobiol. 58(3),393-399(1989).
2. Kumar, S.N., Mohandas, C., and Nambisan, B. Purification, structural elucidation and bioactivity of tryptophan containing diketopiperazines, from Comamonas testosteroni associated with a rhabditid entomopathogenic nematode against major human-pathogenic bacteria Peptides 53(2014),48-58(2014).
3. Furukawa, T., Akutagawa, T., Funatani, H., et al. Cyclic dipeptides exhibit potency for scavenging radicals Bioorg. Med. Chem. 20(6),2002-2009(2012).
4. Naim, M., Nir, S., Spielman, A.I., et al. Hypothesis of receptor-dependent and receptor-independent mechanisms for bitter and sweet taste transduction: Implications for slow taste onset and lingering aftertaste Chemistry of Taste 825,2–17(2002).
5. Zubare-Samuelov, M., Peri, I., Tal, M., et al. Some sweet and bitter tastants stimulate inhibitory pathway of adenylyl cyclase via melatonin and α2-adrenergic receptors in Xenopus laevis melanophores Am. J. Physiol. Cell Physiol. 285(5),C1255-1262(2003).

cyclo(L-leucyl-L-tryptophyl) Preparation Products And Raw materials

Raw materials

Preparation Products

cyclo(L-leucyl-L-tryptophyl) Suppliers

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cyclo(L-leucyl-L-tryptophyl) Cyclo(L-Leu-L-Trp) Cyclo(Trp-Leu) (3S,6S)-3-(1H-indol-3-ylmethyl)-6-(2-methylpropyl)piperazine-2,5-dione cyclo-L-Trp-L-Leu 2,5-Piperazinedione, 3-(1H-indol-3-ylmethyl)-6-(2-methylpropyl)-, (3S,6S)- c(Leu-Trp) 15136-34-2