A peptide with antibacterial and antiviral activities
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Feglymycin

Item No. 28166

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2R)-2-(4-hydroxyphenyl)glycyl-(2R)-2-(3,5-dihydroxyphenyl)glycyl-L-valyl-(2R)-2-(3,5-dihydroxyphenyl)glycyl-(2S)-2-(4-hydroxyphenyl)glycyl-(2R)-2-(3,5-dihydroxyphenyl)glycyl-(2S)-2-(4-hydroxyphenyl)glycyl-(2R)-2-(3,5-dihydroxyphenyl)glycyl-L-valyl-(2R)-2-(3,5-dihydroxyphenyl)glycyl-(2S)-2-(4-hydroxyphenyl)glycyl-L-phenylalanyl-L-aspartic acid
CAS Number
209335-49-9
Molecular Formula
C95H97N13O30
Formula Weight
1900.9
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: solubleDMSO: solubleEthanol: solubleMethanol: soluble
SMILES
OC1=CC=C([C@@H](N)C(N[C@H](C2=CC(O)=CC(O)=C2)C(N[C@@H](C(C)C)C(N[C@H](C3=CC(O)=CC(O)=C3)C(N[C@@H](C4=CC=C(O)C=C4)C(N[C@H](C5=CC(O)=CC(O)=C5)C(N[C@@H](C6=CC=C(O)C=C6)C(N[C@@H](C(N[C@@H](C(C)C)C(N[C@H](C7=CC(O)=CC(O)=C7)C(N[C@@H](C8=CC=C(O)C=C8)C(N[C@H](C(N[C@H](C(O)=O)CC(O)=O)=O)CC9=CC=CC=C9)=O)=O)=O)=O)C%10=CC(O)=CC(O)=C%10)=O)=O)=O)=O)=O)=O)=O)C=C1
InChi Code
InChI=1S/C95H97N13O30/c1-43(2)73(99-90(132)78(50-27-59(113)37-60(114)28-50)101-84(126)72(96)46-10-18-55(109)19-11-46)85(127)106-81(53-33-65(119)40-66(120)34-53)93(135)103-77(49-16-24-58(112)25-17-49)89(131)108-82(54-35-67(121)41-68(122)36-54)94(136)104-76(48-14-22-57(111)23-15-48)88(130)107-79(51-29-61(115)38-62(116)30-51)91(133)100-74(44(3)4)86(128)105-80(52-31-63(117)39-64(118)32-52)92(134)102-75(47-12-20-56(110)21-13-47)87(129)97-69(26-45-8-6-5-7-9-45)83(125)98-70(95(137)138)42-71(123)124/h5-25,27-41,43-44,69-70,72-82,109-122H,26,42,96H2,1-4H3,(H,97,129)(H,98,125)(H,99,132)(H,100,133)(H,101,126)(H,102,134)(H,103,135)(H,104,136)(H,105,128)(H,106,127)(H,107,130)(H,108,131)(H,123,124)(H,137,138)/t69-,70-,72+,73-,74-,75-,76-,77-,78+,79+,80+,81+,82+/m0/s1
InChi Key
QJQKBRUTBCTBKE-OVYRLPCXSA-N
Origin
Bacterium/Streptomyces sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    Feglymycin is a 13-amino acid peptide originally isolated from Streptomyces that has antibacterial and antiviral activities.1 It is active against Gram-positive bacteria (MICs = 32-64 µg/ml) and inhibits HIV viral replication in H9 cells (IC50 = ~5 µM). Feglymycin is also active against clinical isolates of HIV-1 from clades A-D, A/E, and G (EC50s = 0.5-6.7 µM).2 It interacts with gp120 and inhibits HIV-1 NL4.3 binding to human soluble CD4 (EC50 = 4.4 µM) and to CD4+ SupT1 T cells by 74.5% when used at a concentration of 10.5 µM. Feglymycin inhibits the E. coli peptidoglycan biosynthesis enzymes MurA and MurC (Kis = 3.4 and 0.3 µM, respectively) in a noncompetitive manner.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Vértesy, L., Aretz, W., Knauf, M., et al. Feglymycin, a novel inhibitor of the replication of the human immunodeficiency virus. Fermentation, isolation and structure elucidation. J. Antibiot. (Tokyo) 52(4), 374-382 (1999).

    2. Férir, G., Hänchen, A., François, K.O., et al. Feglymycin, a unique natural bacterial antibiotic peptide, inhibits HIV entry by targeting the viral envelope protein gp120. Virology 433(2), 308-319 (2012).

    3. Rausch, S., Hänchen, A., Denisiuk, A., et al. Feglymycin is an inhibitor of the enzymes MurA and MurC of the peptidoglycan biosynthesis pathway. Chembiochem 12(8), 1171-1173 (2011).