Conformationally restricted nucleosides. The reaction of adenosine deaminase with substrates built on a bicyclo[3.1.0]hexane template

Article abstract of DOI:10.1080/15257779908041487

Adenosine deaminase (ADA) can discriminate between two distinct (North and South), conformationally rigid substrate conformers. (N)-methanocarba- 2'dA (4) is deaminated 100 times faster than the antipodal (S)-methanocarba- 2'dA (5), whereas a nonrigid analogue, aristeromycin (6), is deaminated at an intermediate rate. These results are in agreement with crystallographic data from ADA-ribonucleoside complexes showing the furanose ring of the bound purine in a C3'-endo (North) conformation. The data presented here suggests that 4 and 5 are useful probes to ascertain conformational preferences by purine metabolizing enzymes.

Full text of DOI:10.1080/15257779908041487

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Nucleosides and Nucleotides
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Conformationally Restricted
Nucleosides. The Reaction of Adenosine
Deaminase with Substrates Built on a
Bicyclo[3.1.0]hexane Template
a
a
a
Victor E. Marquez , Pamela Russ , Randolph Alonso , Maqbool A.
a
a
b
a
Siddiqui , Kye-Jung Shin , Clifford George , Marc C. Nicklaus
,
a
a
Fang Dai & Harry Ford Jr.
a
Laboratory of Medicinal Chemistry, Division of Basic Sciences ,
National Cancer Institute, National Institutes of Health , Bethesda,
MD, 20892
b
Laboratory for the Structure of Matter, Naval Research
Laboratory , Washington, DC, 20375
Published online: 04 Oct 2006.
To cite this article: Victor E. Marquez , Pamela Russ , Randolph Alonso , Maqbool A. Siddiqui ,
Kye-Jung Shin , Clifford George , Marc C. Nicklaus , Fang Dai & Harry Ford Jr. (1999)
Conformationally Restricted Nucleosides. The Reaction of Adenosine Deaminase with Substrates
Built on a Bicyclo[3.1.0]hexane Template, Nucleosides and Nucleotides, 18:4-5, 521-530, DOI:
10.1080/15257779908041487
To link to this article: http://dx.doi.org/10.1080/15257779908041487
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