Thiazolyl peptide antibiotic nocathiacin I (1) was converted to nocathiacin acid (4) in high yield by treatment with trifluoroacetic anhydride and pyridine in THF at room temperature. Two equipotent water-soluble amide analogues of nocathiacin I were readily prepared from this important and versatile carboxylic acid intermediate under mild peptide coupling conditions. The present method is useful for chemical derivatization of complex natural products that contain C-terminal dehydroalanine.
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Separation of structurally similar nocathiacin analogues by reversed phase chromatography.
J Chromatogr A
April 2010
Laboratory of Chemical Biology, China Pharmaceutical University, Nanjing, China.
The complete separation of structurally similar compounds has been a challenge due mainly to their similarity on physical and chemical properties. In the present study, a simple and effective chromatographic method to separate and purify nocathiacin acid from its structural analogue nocathiacin I was developed. After evaluating mobile phase compositions on the retention characteristics by reversed phase high-performance liquid chromatography (HPLC), the elution order of nocathiacin I and nocathiacin acid was completely reversed, and the resolution value between the two analogues was improved, by varying pH value and ionic strength, to greater than 10 from merged peaks under initial conditions.
View Article and Find Full Text PDFMicrobial generation of nocathiacin acid from nocathiacin I.
Bioresour Technol
May 2010
Laboratory of Chemical Biology, China Pharmaceutical University, 24 Tongjia Street, Nanjing, Jiangsu Province 210009, People's Republic of China.
Microbial generation of nocathiacin acid from nocathiacin I by manipulating enzymatic activities related to C-terminal dehydroalanine hydrolysis in Amycolatopsis fastidiosa LCB1001 was investigated by comparing the effects of various factors including metal ions, amino acid precursors and starting pH on the transformation. CuCl(2) and cysteine significantly increased bioconversion yields, and starting pH and time were also major factors affecting the product yield. Under optimal conditions, the yield of nocathiacin acid was increased from 10.
View Article and Find Full Text PDFConversion of nocathiacin I to nocathiacin acid by a mild and selective cleavage of dehydroalanine.
J Org Chem
September 2007
Merck Research Laboratories, Rahway, NJ 07065, USA.
Thiazolyl peptide antibiotic nocathiacin I (1) was converted to nocathiacin acid (4) in high yield by treatment with trifluoroacetic anhydride and pyridine in THF at room temperature. Two equipotent water-soluble amide analogues of nocathiacin I were readily prepared from this important and versatile carboxylic acid intermediate under mild peptide coupling conditions. The present method is useful for chemical derivatization of complex natural products that contain C-terminal dehydroalanine.
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