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cyclo(L-leucyl-L-tryptophyl)

Product Name
cyclo(L-leucyl-L-tryptophyl)
CAS No.
15136-34-2
Chemical Name
cyclo(L-leucyl-L-tryptophyl)
Synonyms
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
Formula Weight
299.37
MOL File
15136-34-2.mol
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cyclo(L-leucyl-L-tryptophyl) Property

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)
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Cayman Chemical
Product number
24942
Product name
Cyclo(L-Leu-L-Trp)
Purity
≥95%
Packaging
5mg
Price
$242
Updated
2024/03/01
Cayman Chemical
Product number
24942
Product name
Cyclo(L-Leu-L-Trp)
Purity
≥95%
Packaging
25mg
Price
$846
Updated
2024/03/01
Biosynth Carbosynth
Product number
FC108311
Product name
Cyclo(-Leu-Trp)
Packaging
2g
Price
$949.56
Updated
2021/12/16
Biosynth Carbosynth
Product number
FC108311
Product name
Cyclo(-Leu-Trp)
Packaging
100mg
Price
$91
Updated
2021/12/16
Biosynth Carbosynth
Product number
FC108311
Product name
Cyclo(-Leu-Trp)
Packaging
250mg
Price
$180
Updated
2021/12/16
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cyclo(L-leucyl-L-tryptophyl) Chemical Properties,Usage,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

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

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15136-34-2, cyclo(L-leucyl-L-tryptophyl)Related Search:

CYCLO(-PHE-TRP) CYCLO(-D-LEU-D-PRO)

  • 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)-
  • 15136-34-2