A cyclic thiopeptide bacterial metabolite
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Geninthiocin A

Item No. 28125

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
L-threonyl-2-[(1Z)-1-amino-1-propen-1-yl]-4-oxazolecarbonyl-2,3-didehydroalanyl-3-methyl-L-threonyl-2-(1-aminoethenyl)-5-methyl-4-oxazolecarbonyl-2,3-didehydroalanyl-6-[2-(1-aminoethenyl)-4-oxazolyl]-5-(4-carboxy-2-thiazolyl)-2-pyridinecarbonyl-2,3-didehydroalanyl-2,3-didehydro-alaninamide (7→1)-lactam
CAS Number
158792-27-9
Molecular Formula
C50H49N15O15S
Formula Weight
1132.1
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: Slightly soluble
SMILES
O=C(N[C@]([C@@H](C)O)([H])C(N/C(C1=NC(C(NC2=C)=O)=CO1)=C\C)=O)C3=CSC(C4=C(C5=COC(C(NC(C(NC(C6=C(C)OC(C(NC([C@H](C(O)(C)C)NC2=O)=O)=C)=N6)=O)=C)=O)=C)=N5)N=C(C(NC(C(NC(C(N)=O)=C)=O)=C)=O)C=C4)=N3
InChi Code
InChI=1S/C50H49N15O15S/c1-12-27-48-61-30(16-79-48)41(72)54-21(5)39(70)65-35(50(10,11)77)45(76)57-23(7)47-64-33(25(9)80-47)44(75)55-20(4)38(69)56-22(6)46-60-29(15-78-46)34-26(49-62-31(17-81-49)42(73)63-32(24(8)66)43(74)59-27)13-14-28(58-34)40(71)53-19(3)37(68)52-18(2)36(51)67/h12-17,24,32,35,66,77H,2-7H2,1,8-11H3,(H2,51,67)(H,52,68)(H,53,71)(H,54,72)(H,55,75)(H,56,69)(H,57,76)(H,59,74)(H,63,73)(H,65,70)/b27-12-/t24-,32+,35-/m1/s1
InChi Key
JNUIXQXFKIJDIV-AQJAKWKPSA-N
Origin
Bacterium/Streptomyces sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Geninthiocin A is a cyclic thiopeptide bacterial metabolite originally isolated from Streptomyces sp. DD84.1 It is active against a variety of Gram-positive bacteria (MICs = 0.2-4 µg/ml), the Gram-negative bacterium C. violaceum (MIC = 19 µg/ml), and the fungus M. hiemalis (MIC = 38 µg/ml).2 Geninthiocin A also induces tipA promoter transcription with a minimum induction concentration of 1.2 ng/ml.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Yun, B.-S., Hidaka, T., Furihata, K., et al. Microbial metabolites with tipA promoter inducing activity. II. Geninthiocin, a novel thiopeptide produced by Streptomyces sp. DD84. J. Antibiot. (Tokyo) 47(9), 969-975 (1994).

    2. Iniyan, A.M., Sudarman, E., Wink, J., et al. Ala-geninthiocin, a new broad spectrum thiopeptide antibiotic, produced by a marine Streptomyces sp. ICN19. J. Antibiot. (Tokyo) 72(2), 99-105 (2019).