A cyclic heptapeptide containing GABA
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Unguisin A

Item No. 23878

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
cyclo(D-alanyl-D-tryptophyl-4-aminobutanoyl-D-alanyl-D-valyl-L-phenylalanyl-D-valyl)
CAS Number
226956-06-5
Molecular Formula
C40H54N8O7
Formula Weight
758.9
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: solubleDMSO: solubleEthanol: solubleMethanol: soluble
SMILES
O=C(NCCCC(N[C@H](C)C1=O)=O)[C@@H](CC2=CNC3=CC=CC=C32)NC([C@@H](C)NC([C@](C(C)C)([H])NC([C@H](CC4=CC=CC=C4)NC([C@@H](C(C)C)N1)=O)=O)=O)=O
InChi Code
InChI=1S/C40H54N8O7/c1-22(2)33-39(54)44-25(6)35(50)45-31(20-27-21-42-29-16-11-10-15-28(27)29)37(52)41-18-12-17-32(49)43-24(5)36(51)47-34(23(3)4)40(55)46-30(38(53)48-33)19-26-13-8-7-9-14-26/h7-11,13-16,21-25,30-31,33-34,42H,12,17-20H2,1-6H3,(H,41,52)(H,43,49)(H,44,54)(H,45,50)(H,46,55)(H,47,51)(H,48,53)/t24-,25-,30+,31-,33-,34-/m1/s1
InChi Key
JLLVQPKAQVOYFS-KVOZXUITSA-N
Origin
Fungus/Aspergillus unguis
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Unguisin A is a cyclic heptapeptide originally isolated from the marine fungus E. unguis whose structure is comprised of amino acids and GABA.1 It binds to phosphate, pyrophosphate, and chloride but has no effect on chloride transport in a liposome-based assay.2 It exhibited moderate antibacterial activity against S. aureus and V. parahaemolyticus in one assay but no activity against a variety of bacteria, including S. aureus, in another.1,2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Malmstrom, J. Unguisins A and B: New cyclic peptides from the marine-derived fungus Emericella unguis. J. Nat. Prod. 62(5), 787-789 (1999).

    2. Ariawan, A.D., Webb, J.E.A., Howe, E.N.W., et al. Cyclic peptide unguisin A is an anion receptor with high affinity for phosphate and pyrophosphate. Org. Biomol. Chem. 15(14), 2962-2967 (2017).