A cyclic depsipeptide with antibacterial activity
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Griselimycin

Item No. 39306

Technical Information
Formal Name
N-acetyl-N-methyl-L-valyl-(4R)-4-methyl-L-prolyl-N-methyl-L-threonyl-L-leucyl-(4R)-4-methyl-L-prolyl-L-leucyl-N-methyl-L-valyl-L-prolyl-N-methyl-D-leucyl-glycine, (10→3)-lactone
CAS Number
26034-16-2
Synonyms
  • NSC 246122
Molecular Formula
C57H96N10O12
Formula Weight
Purity
≥98%
A solid
SMILES
CN(C([C@@H]1C[C@@H](C)CN1C([C@H](C(C)C)N(C)C(C)=O)=O)=O)[C@@H]([C@@H](C)OC(CNC([C@H](N(C([C@]2([H])CCCN2C([C@@H](N(C)C([C@@H](NC3=O)CC(C)C)=O)C(C)C)=O)=O)C)CC(C)C)=O)=O)C(N[C@@H](CC(C)C)C(N4[C@@]3([H])C[C@@H](C)C4)=O)=O
InChi Code
InChI=1S/C57H96N10O12/c1-30(2)22-39-52(73)63(17)47(34(9)10)56(77)65-21-19-20-41(65)54(75)62(16)42(24-32(5)6)49(70)58-27-45(69)79-37(13)48(51(72)60-40(23-31(3)4)53(74)66-28-35(11)25-43(66)50(71)59-39)64(18)55(76)44-26-36(12)29-67(44)57(78)46(33(7)8)61(15)38(14)68/h30-37,39-44,46-48H,19-29H2,1-18H3,(H,58,70)(H,59,71)(H,60,72)/t35-,36-,37-,39+,40+,41+,42-,43+,44+,46+,47+,48+/m1/s1
InChi Key
JSNIAKPKPNJUEP-BHYOTPSJSA-N
Origin
Bacterium/Streptomyces muensis
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    Griselimycin is a cyclic depsipeptide that has been found in Streptomyces and has antibacterial activity.1,2 It is active against M. tuberculosis strain H37Rv (MICs = 1-1.2 and 6.2 µg/ml in liquid culture and RAW 264.7 macrophages, respectively) but associated with resistance.2 Griselimycin inhibits the protein-protein interaction between the M. smegmatis DNA polymerase sliding clamp, DnaN, and M. smegmatis DNA polymerase, leading to inhibition of DNA replication.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Terlain, B., and Thomas, J.P. Structure of griselimycin, a polypeptide antibiotic extracted from streptomyces cultures. C.R. Acad. Sci. C Chim. 269(24), 1546-1549 (1969).

    2. Kling, A., Lukat, P., Almeida, D.V., et alTargeting DnaN for tuberculosis therapy using novel griselimycins. Science 348(6239), 1106-1112 (2015).