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Cyclic phosphates of formycin.

O Makabe, A Miyadera, M Kinoshita

The Journal of Antibiotics

|May 1, 1978

Summary

Researchers synthesized novel formycin derivatives, including N1- and N2-isopropylformycin and cyclic phosphates. These modified formycins demonstrated resistance to adenosine deaminase, suggesting potential therapeutic applications.

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Area of Science:

Medicinal Chemistry
Nucleoside Analog Synthesis

Background:

Formycin is a nucleoside antibiotic with potential biological activities.
Adenosine deaminase (ADA) is an enzyme that can inactivate nucleoside analogs.
Modifying nucleoside structures can alter their susceptibility to enzymatic degradation.

Purpose of the Study:

To synthesize novel formycin derivatives with modifications at the N1 or N2 positions and on the ribose moiety.
To investigate the impact of these structural modifications on the stability of formycin against adenosine deaminase.
To explore the potential of these derivatives as resistant nucleoside analogs.

Main Methods:

Chemical synthesis of N1- and N2-isopropylformycin.
Preparation of formycin 3',5'-cyclic and 2',3'-cyclic phosphates.
Synthesis of N-methyl and N-isopropyl derivatives of the cyclic phosphates.
Assay of synthesized compounds for resistance to adenosine deaminase.

Main Results:

Successful synthesis of N1- and N2-isopropylformycin and various cyclic phosphate derivatives.
Demonstrated that bulky alkyl substitution at N1 or N2 renders formycin resistant to adenosine deaminase.
Showed that cyclic phosphorylation of the ribose moiety also confers resistance to adenosine deaminase.

Conclusions:

Structural modifications, specifically bulky alkyl substitution or cyclic phosphorylation, can effectively confer adenosine deaminase resistance to formycin.
These findings open avenues for developing more stable and potentially therapeutic formycin-based nucleoside analogs.

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