Acid promoted transformations of fluorescent luminarosine and its 2'-modified analogues

• Autorzy: Burdzy A. , Skalski B. , Paszyc S. , Popenda M. , Adamiak R.W.
• Języki publikacji: EN

Abstrakty

EN

The susceptibility of highly fluorescent luminarine nucleosides to acid promoted anomerization reactions has been studied in order to select a derivative with suitable properties for chemical synthesis of luminarine-labeled oligo(deoxy)ribonucleotides. Both O-acetylated derivatives Ia-c and parent luminarosine IIa, as well as 2'-O-meth-ylluminarosine IIb, and 2'-deoxyluminarosine IIc undergo anomerization at pH = 4 however, at considerably different velocities. In the case of O-protected nucleosides (Ia-c), the anomerization leads to an equilibrium mixture of respective b and a furanosides, the rate and extent of anomerization decreasing in the following order: Ic >> Ia > Ib. Parent nucleosides (IIa-c) bearing free hydroxyls are generally more susceptible to anomerization than the O-acetylated derivatives but a similar order of reactivity (IIc >> IIa > IIb) is observed. In each case, a complex mixture containing both b and a ribopyranosyl and -furanosyl forms is formed. Their structure and anomeric configuration have been proved by 1H and 13C NMR spectroscopy. The results point to 2'-O-methylluminarosine as the fluorophore of choice for further derivatization and chemical introduction into oligo(deoxy)ribonucleotides.

Słowa kluczowe

EN

fluorescent luminarosine; 2'-modified analogue; oligo[deoxy]ribonucleotide; luminarosine analogue

• Wydawca: -
• Czasopismo: Acta Biochimica Polonica
• Rocznik: 1998
• Tom: 45
• Numer: 4
• Opis fizyczny: p.941-948,fig.

Twórcy

autor

Burdzy A.

• Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznan, Poland

autor

Skalski B.

autor

Paszyc S.

autor

Popenda M.

autor

Adamiak R.W.

Bibliografia

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