A mixture of tunicamycin 16:1 structural isomers
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Tunicamycin 16:1 Mixture

Item No. 28357

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Molecular Formula
C39H64N4O16
Formula Weight
844.9
Purity
≥95% (mixture of isomers)
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlDMSO:PBS (pH 7.2) (1:3): 0.25 mg/ml
λmax
260 nm
SMILES
CC(N[C@H]1[C@@H](O[C@@]2([H])[C@H](NC(/C=C/CCCCCCCCCCC(C)C)=O)[C@@H](O)[C@@H](O)[C@@H](C[C@@H](O)[C@@H]3[C@@H](O)[C@@H](O)[C@H](N4C=CC(NC4=O)=O)O3)O2)O[C@H](CO)[C@@H](O)[C@@H]1O)=O
InChi Code
InChI=1S/C39H64N4O16/c1-20(2)14-12-10-8-6-4-5-7-9-11-13-15-25(47)41-28-32(52)29(49)23(56-38(28)59-37-27(40-21(3)45)31(51)30(50)24(19-44)57-37)18-22(46)35-33(53)34(54)36(58-35)43-17-16-26(48)42-39(43)55/h13,15-17,20,22-24,27-38,44,46,49-54H,4-12,14,18-19H2,1-3H3,(H,40,45)(H,41,47)(H,42,48,55)/b15-13+/t22-,23-,24-,27-,28-,29+,30-,31-,32-,33+,34-,35-,36-,37-,38+/m1/s1
InChi Key
ZOCXUHJGZXXIGQ-NPXWYGMKSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    Tunicamycin 16:1 is a mixture of tunicamycin structural isomers that contain a 16-carbon N-acyl chain with variable branching patterns. The N-acyl chain incorporated into tunicamycins, like tunicamycin 16:1, is derived from the same pool of cellular branched-chain fatty acids (BCFAs) in Streptomyces and directly impacts the biological activity of each individual tunicamycin variant.1,2,3 Purified tunicamycin 16:1 with the iso branching configuration inhibits bacterial phospho-MurNAc-pentapeptide transferase (MraY) with an IC50 value of 0.11 µM.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Price, N.P.J., Jackson, M.A., Hartman, T.M., et al. Branched chain lipid metabolism as a determinant of the N-Acyl variation of Streptomyces natural products. ACS Chem. Biol. 16(1), 116-124 (2021).

    2. Hering, J., Dunevall, E., Snijder, A., et al. Exploring the active site of the antibacterial target MraY by modified tunicamycins. ACS Chem Biol. 15(11), 2885-2895 (2020).

    3. Duksin, D., and Mahoney, W.C. Relationship of the structure and biological activity of the natural homologues of tunicamycin. The Journal of Biological Chemisty 257(6), 3105-3109 (1982).