Synthesis and properties of oligonucleotides containing 8-bromo-2'-deoxyguanosine.

نویسندگان

  • C Fàbrega
  • M J Macías
  • R Eritja
چکیده

The preparation of oligonucleotides containing 8-bromo-2'-deoxyguanosine is described. Substitution of G by 8-bromoguanine on an alternating CG decamer stabilizes the Z-form in such a way that the B-form was not observed. Melting temperatures showed that duplexes in which 8-bromo-2'-deoxyguanosine paired with natural bases were much less stable.

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

2'-Deoxyimmunosine: stereoselective synthesis, base pairing and duplex stability of oligonucleotides containing 8-oxo-7-thiaguanine.

Oligonucleotides containing 7-thia-8-oxoguanine represent a new class of molecules in which sulfur replaces the 7-nitrogen of a purine base. The monomeric 7-thia-8-oxoguanine 2'-deoxyribonucleoside (2'-deoxyimmunosine, 4) was prepared by nucleobase anion glycosylation in a regio- and stereoselective way employing 5-{[(di-n-butylamino)methylidene]amino}thiazolo[4,5-d]pyrimidine-2,7(3H,6H)-dione ...

متن کامل

Propynyl groups in duplex DNA: stability of base pairs incorporating 7-substituted 8-aza-7-deazapurines or 5-substituted pyrimidines.

Oligonucleotides incorporating the 7-propynyl derivatives of 8-aza-7-deaza-2'-deoxyguanosine (3b) and 8-aza-7-deaza-2'-deoxyadenosine (4b) were synthesized and their duplex stability was compared with those containing the 5-propynyl derivatives of 2'-deoxycytidine (1) and 2'-deoxyuridine (2). For this purpose phosphoramidites of the 8-aza- 7-deazapurine (pyrazolo[3,4-d]pyrimidine) nucleosides w...

متن کامل

The effect of the 2-amino group of 7,8-dihydro-8-oxo-2′-deoxyguanosine on translesion synthesis and duplex stability

Replication of DNA containing 7,8-dihydro-8-oxo-2'-deoxyguanosine (OxodG) gives rise to G --> T transversions. The syn-isomer of the lesion directs misincorporation of 2'-deoxyadenosine (dA) opposite it. We investigated the role of the 2-amino substituent on duplex thermal stability and in replication using 7,8-dihydro-8-oxo-2'-deoxyinosine (OxodI). Oligonucleotides containing OxodI at defined ...

متن کامل

Solid-phase synthesis of DNA fragments containing the modified base 7-hydro-8-oxo-2'-deoxyguanosine.

The 5'-(4,4'-dimethoxytrityl) protected 3'-(2-cyanoethoxy)-N,N-diisopropylphosphoramidite of 7-hydro-8-oxo-2'-deoxy-guanosine, the exocyclic amino and lactam functions of which are protected with acetyl and diphenylcarbamoyl groups, respectively, has been prepared from the 8-bromo derivatives of deoxy- and riboguanosine. This synthon, in combination with standard d-nucleoside 3'-(2-cyanoethoxy)...

متن کامل

7-Deaza-2,8-diazaadenine containing oligonucleotides: synthesis, ring opening and base pairing of 7-halogenated nucleosides

Oligonucleotides containing 7-bromo-7-deaza-2,8-diaza-2 0-deoxyadenosine (3) and 5-amino-3-bromo-4-carbamoyl-1-(2 0deoxy-b-D-erythro-pentofuranosyl)pyrazole (4) were synthesized. Compound 3 was prepared from 7-bromo-8-aza-7-deaza-2 0-deoxyadenosine (5) via the 1,N-etheno derivative 6 and was converted into the phosphoramidite 11. The 7-bromo substituent of 3 increases oligonucleotide duplex sta...

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:
  • Nucleosides, nucleotides & nucleic acids

دوره 20 3  شماره 

صفحات  -

تاریخ انتشار 2001