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Absolute Configurations of Griseorhodins A and C

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Publisher Elsevier
Specialty Chemistry
Date 2018 Mar 6
PMID 29503481
Citations 4
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Abstract

The known antibiotic and cytotoxic compounds griseorhodin A () and griseorhodin C () were produced in solid culture by AB10, which was isolated from the leaf-cutter ant . Their absolute configurations were unambiguously established as 6,6a,7,8 and 6,6a,7,8, respectively, using vibrational circular dichroism (VCD) and density functional theory (DFT) calculations.

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References
1.
Yunt Z, Reinhardt K, Li A, Engeser M, Dahse H, Gutschow M . Cleavage of four carbon-carbon bonds during biosynthesis of the griseorhodin a spiroketal pharmacophore. J Am Chem Soc. 2009; 131(6):2297-305. DOI: 10.1021/ja807827k. View

2.
Eckardt K, Tresselt D, Ihn W . The structure of the antibiotic griseorhodin C. J Antibiot (Tokyo). 1978; 31(10):970-3. DOI: 10.7164/antibiotics.31.970. View

3.
Panzone G, Trani A, Ferrari P, Gastaldo L, Colombo L . Isolation and structure elucidation of 7,8-dideoxy-6-oxo-griseorhodin C produced by Actinoplanes ianthinogenes. J Antibiot (Tokyo). 1997; 50(8):665-70. DOI: 10.7164/antibiotics.50.665. View

4.
Ueno T, Takahashi H, Oda M, Mizunuma M, Yokoyama A, Goto Y . Inhibition of human telomerase by rubromycins: implication of spiroketal system of the compounds as an active moiety. Biochemistry. 2000; 39(20):5995-6002. DOI: 10.1021/bi992661i. View

5.
Stroshane R, Chan J, Rubalcaba E, GARRETSON A, Aszalos A, Roller P . Isolation and structure elucidation of a novel griseorhodin. J Antibiot (Tokyo). 1979; 32(3):197-204. DOI: 10.7164/antibiotics.32.197. View