A cyclic dipeptide
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Isomer(s)
29320Fellutanine A
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Cyclo(L-Trp-L-Trp)

Item No. 23494

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3S,6S-bis(1H-indol-3-ylmethyl)-2,5-piperazinedione
CAS Number
20829-55-4
Synonyms
  • Cyclic dioxopiperazine-L-tryptophan-L-tryptophan
Molecular Formula
C22H20N4O2
Formula Weight
372.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:10): 0.1 mg/mlEthanol: 5 mg/ml
λmax
221, 281, 291 nm
SMILES
O=C([C@H](CC1=CNC2=C1C=CC=C2)N3)N[C@@H](CC4=CNC5=C4C=CC=C5)C3=O
InChi Code
InChI=1S/C22H20N4O2/c27-21-19(9-13-11-23-17-7-3-1-5-15(13)17)25-22(28)20(26-21)10-14-12-24-18-8-4-2-6-16(14)18/h1-8,11-12,19-20,23-24H,9-10H2,(H,25,28)(H,26,27)/t19-,20-/m0/s1
InChi Key
DNHODRZUCGXYKU-PMACEKPBSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    50 mg

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    500 mg

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    Product Description

    Cyclo(L-Trp-L-Trp) is a cyclic dipeptide that has been used as a substrate for indole prenyltransferases in the synthesis of mono- and diprenylated indolines.1,2 It has antibacterial activity and inhibits growth of 41 out of 49 strains of multidrug resistant A. baumannii (MICs = 12.5-25 µg/ml) as well as B. subtilis, M. luteus, S. aureus, S. cerevisiae, A. niger, and C. albicans (MICs = 12.5-50 µg/ml).3 Prenylated forms of cyclo(L-Trp-L-Trp) are cytotoxic against human leukemia and ovarian cell lines.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Yin, W.-B., Xie, X.-L., Matuschek, M., et al. Reconstruction of pyrrolo[2,3-b]indoles carrying an alpha-configured reverse C3-dimethylallyl moiety by using recombinant enzymes. Org. Biomol. Chem. 8(5), 1133-1141 (2010).

    2. Zou, H.-X., Xie, X.-L., Linne, U., et al. Simultaneous C7- and N1-prenylation of cyclo-L-Trp-L-Trp catalyzed by a prenyltransferase from Aspergillus oryzae. Org. Biomol. Chem. 8(13), 3037-3044 (2010).

    3. Lee, K.-H., Kim, K.-W., and Rhee, K.-H. Identification of Streptomyces sp. KH29, which produces an antibiotic substance processing an inhibitory activity against multidrug-resistant Acinetobacter baumannii. J. Microbiol. Biotechnol. 20(12), 1672-1676 (2010).

    4. Wollinsky, B., Ludwig, L., Hamacher, A., et al. Prenylation at the indole ring leads to a significant increase of cytotoxicity of tryptophan-containing cyclic dipeptides. Bioorg. Med. Chem. Lett. 22(12), 3866-3869 (2012).