An antibiotic and derivative of tunicamycin
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TunR2

Item No. 31538

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-((2S,3R,4R,5R,6R)-2-(((2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-6-((R)-2-((2R,3S,4R,5R)-5-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)-2-hydroxyethyl)-4,5-dihydroxytetrahydro-2H-pyran-3-yl)-12-methyltridecanamide
Molecular Formula
C39H68N4O16 (for TunR2 16:0)
Purity
≥95% (mixture of congeners)
Formulation (Request formulation change)
A crystalline solid
SMILES
CC(N[C@H]1[C@@H](O[C@H]2[C@H](NC(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](N4CCC(NC4=O)=O)O3)O2)O[C@H](CO)[C@@H](O)[C@@H]1O)=O.CC(N[C@H]5[C@@H](O[C@H]6[C@H](NC(CCCCCCCCCCCC(C)C)=O)[C@@H](O)[C@@H](O)[C@@H](C[C@@H](O)[C@@H]7[C@@H](O)[C@@H](O)[C@H](N8CCC(NC8=O)=O)O7)O6)O[C@H](CO)[C@@H](O)[C@@H]5O)=O.CC(N[C@H]9[C@@H](O[C@H]%10[C@H](NC(CCCCCCCCCCCCC(C)C)=O)[C@@H](O)[C@@H](O)[C@@H](C[C@@H](O)[C@@H]%11[C@@H](O)[C@@H](O)[C@H](N%12CCC(NC%12=O)=O)O%11)O%10)O[C@H](CO)[C@@H](O)[C@@H]9O)=O.CC(N[C@H]%13[C@@H](O[C@H]%14[C@H](NC(CCCCCCCCCCCCCC(C)C)=O)[C@@H](O)[C@@H](O)[C@@H](C[C@@H](O)[C@@H]%15[C@@H](O)[C@@H](O)[C@H](N%16CCC(NC%16=O)=O)O%15)O%14)O[C@H](CO)[C@@H](O)[C@@H]%13O)=O
InChi Code
InChI=1S/C40H70N4O16.C39H68N4O16.C38H66N4O16.C37H64N4O16/c1-21(2)15-13-11-9-7-5-4-6-8-10-12-14-16-26(48)42-29-33(53)30(50)24(57-39(29)60-38-28(41-22(3)46)32(52)31(51)25(20-45)58-38)19-23(47)36-34(54)35(55)37(59-36)44-18-17-27(49)43-40(44)56;1-20(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;1-19(2)13-11-9-7-5-4-6-8-10-12-14-24(46)40-27-31(51)28(48)22(55-37(27)58-36-26(39-20(3)44)30(50)29(49)23(18-43)56-36)17-21(45)34-32(52)33(53)35(57-34)42-16-15-25(47)41-38(42)54;1-18(2)12-10-8-6-4-5-7-9-11-13-23(45)39-26-30(50)27(47)21(54-36(26)57-35-25(38-19(3)43)29(49)28(48)22(17-42)55-35)16-20(44)33-31(51)32(52)34(56-33)41-15-14-24(46)40-37(41)53/h21,23-25,28-39,45,47,50-55H,4-20H2,1-3H3,(H,41,46)(H,42,48)(H,43,49,56);20,22-24,27-38,44,46,49-54H,4-19H2,1-3H3,(H,40,45)(H,41,47)(H,42,48,55);19,21-23,26-37,43,45,48-53H,4-18H2,1-3H3,(H,39,44)(H,40,46)(H,41,47,54);18,20-22,25-36,42,44,47-52H,4-17H2,1-3H3,(H,38,43)(H,39,45)(H,40,46,53)/t23-,24-,25-,28-,29-,30+,31-,32-,33-,34+,35-,36-,37-,38-,39+;22-,23-,24-,27-,28-,29+,30-,31-,32-,33+,34-,35-,36-,37-,38+;21-,22-,23-,26-,27-,28+,29-,30-,31-,32+,33-,34-,35-,36-,37+;20-,21-,22-,25-,26-,27+,28-,29-,30-,31+,32-,33-,34-,35-,36+/m1111/s1
InChi Key
YYDGSKSHTWTNMN-NUYGKJRVSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

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    Product Description

    TunR2 is an antibiotic and derivative of tunicamycin (Item No. 11445).1 It is active against B. subtilis (MIC = 0.3 µg/ml) and increases the efficacy of the β-lactam antibiotics oxacillin (Item No. 23954), methicillin (Item No. 21007), and penicillin G (Item No. 21615) against B. subtilis when used at a concentration of 0.4 μg/ml. Unlike tunicamycin, TunR2 is non-toxic to S. cerevisiae (MIC = >10 μg/ml) and does not inhibit glycosylation in a protein N-glycosylation assay. TunR2 also has reduced antiproliferative activity against MDA-MB-231 and CHO cells compared with tunicamycin.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Price, N.P., Hartman, T.M., Li, J., et al. Modified tunicamycins with reduced eukaryotic toxicity that enhance the antibacterial activity of β-lactams. J. Antibiot. (Tokyo) 70(11), 1070-1077 (2017).