7-Demethylpiericidin A1

7-Demethylpiericidin A1

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Category Antibiotics
Catalog number BBF-00832
CAS
Molecular Weight 401.54
Molecular Formula C24H35NO4

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Description

7-Demethylpiericidin A1 is a pierceridin antibiotic produced by Streptomyces sp. SN-198. It has antifungal and gram-negative bacteria activity.

Specification

IUPAC Name 2-[(2E,5E,7E,9R,10R,11E)-10-hydroxy-3,9,11-trimethyltrideca-2,5,7,11-tetraenyl]-5,6-dimethoxy-3-methyl-1H-pyridin-4-one
Canonical SMILES CC=C(C)C(C(C)C=CC=CCC(=CCC1=C(C(=O)C(=C(N1)OC)OC)C)C)O
InChI InChI=1S/C24H35NO4/c1-8-17(3)21(26)18(4)13-11-9-10-12-16(2)14-15-20-19(5)22(27)23(28-6)24(25-20)29-7/h8-11,13-14,18,21,26H,12,15H2,1-7H3,(H,25,27)/b10-9+,13-11+,16-14+,17-8+/t18-,21+/m1/s1
InChI Key HVSNZEPHFYYIKC-YIOFYXMNSA-N

Properties

Appearance Yellow Oil
Antibiotic Activity Spectrum Gram-negative bacteria; fungi

Reference Reading

1. Titanium(II)-mediated cyclizations of (silyloxy)enynes: a total synthesis of (-)-7-demethylpiericidin A1
Katie A Keaton, Andrew J Phillips J Am Chem Soc. 2006 Jan 18;128(2):408-9. doi: 10.1021/ja057434k.
A concise total synthesis of 7-demethylpiericidin A1 has been completed. The synthesis features a titanium(II)-mediated cyclization of a (silyloxy)enyne as the key step and proceeds in nine steps from tiglic aldehyde.

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* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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