Synthesis of 5-(6-hydroxy-7H-purine-8-ylthio)- 2-(N-hydroxyformamido)pentanoic acid

نویسندگان

  • Yanmei Zhang
  • Greg Elliot
  • Adrian Saldanha
  • Igor Tsigelny
  • Dennis Carson
  • Wolf Wrasidlo
چکیده

We have developed a synthetic route for the preparation of a hybrid bisubstrate small molecule based on a nucleoside. A prototype compound was designed and docked into the catalytic domain of the AdSS enzyme bridging the region between the magnesium center of the protein to the nucleoside region. The synthesis involves coupling a brominated peptide fragment capable of complexing magnesium to a thiolated nucleoside to obtain the hybrid model compound.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Facile synthesis of 9-substituted 9-deazapurines as potential purine nucleoside phosphorylase inhibitors.

A facile synthesis of 9-substituted 9-deazapurines as potential inhibitors of purine nucleoside phosphorylase has been achieved by the direct Friedel-Crafts aroylation or arylmethylation of 9-deazapurines using trifluoromethanesulfonic acid as catalyst. The aroylated 9-deazapurines could be transformed into the corresponding 9-aryimethyl derivatives by the Wolff-Kishner reaction. A novel synthe...

متن کامل

6-Chloropurine and 6-chlorouric acid as substrates and inhibitors of purine-oxidizing enzymes.

Various examples of oxidation of purine molecules in positions 8 and 2 by xanthine oxidase have been reported. The conversions of the natural purine substrates, xanthine and hypoxanthine to uric acid (I) and of adenine to 2,8-dihydroxy-6-aminopurine, are well known. The oxidation of the purine antimetabolites, 6-mercaptopurine to 6-thiouric acid (2)) 2,6-diaminopurine to 2,6-diamino-6-hydroxy p...

متن کامل

DFT energy surfaces for aminopurine homodimers and their conjugate acid ions.

Dimers of free nucleobases with their conjugate acid ions can be assigned to either of two categories: protonated dimers or proton-bound dimers. In the former, the extra proton attaches to a lone pair of a neutral dimer. In the latter, the extra proton is situated between two lone pairs and participates in a proton bridge. In general, proton-bound dimers are found to be more tightly held togeth...

متن کامل

Synthesis of 3-(4-Chloro-2-methoxy-7H-pyrrolo[2,3-d]-pyrimidin-7-yl)propanoic acid – An N(9)-Functionalized 7-Deazapurine

Regioselective N-alkylation of 4-chloro-2-methoxy-7H-pyrrolo[2,3d]pyrimidine (6) with ethyl 3-bromopropionate under liquid-liquid phase-transfer reaction conditions gave the ester 7a. Its saponification yielded the acid 7b. The logP values of a series of N(9)-functionalized purines and purine isosteres were calculated.

متن کامل

5-(6-Hydroxy-2,5,7,8-tetramethylchroman-2-yl)-2-methyl-pentanoic Acid Methyl Ester

A natural diastereomeric mixture of 5-(6-hydroxy-2,5,7,8-tetramethyl-chroman2-yl)-2-methyl-pentanoic acid methyl ester (1), was isolated from the soft coral Sinularia arborea. The structure of 1 was elucidated by spectroscopic methods and 1 displayed a significantly inhibitory effect on the generation of superoxide anion by human neutrophils.

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:

دوره 6  شماره 

صفحات  -

تاریخ انتشار 2010