Structure–reactivity relationship for the cobalt(III) complex-catalysed hydrolysis of adenosine 3′,5′-cyclic monophosphate 1

1997 ◽  
pp. 75-78 ◽  
Author(s):  
Makoto Komiyama ◽  
Jun Sumaoka ◽  
Koji Yonezawa ◽  
Yoichi Matsumoto ◽  
Morio Yashiro
Keyword(s):  
Cyclic Monophosphate ◽  
Structure Reactivity Relationship ◽  
Hydrolysis Of

Iodine(III)-Mediated Oxidative Hydrolysis of Haloalkenes: Investigation of the Effect of Iodine(III) Reagents

Synthesis ◽  
2017 ◽  
Vol 49 (13) ◽  
pp. 2928-2932
Author(s):  
Claude Legault ◽  
Robin Dagenais ◽  
Antoine Lauriers
Keyword(s):  
Waste Products ◽  
Vinyl Halides ◽  
Good Substrate ◽  
Synthetic Transformation ◽  
Relationship Study ◽  
Structure Reactivity Relationship ◽  
Hydrolysis Of

The iodine(III)-mediated oxidative transposition of vinyl halides to the corresponding α-halo ketones has been recently reported. The method is high yielding and offers good substrate scope. The investigation of other iodine(III) reagents to promote this reaction is described. The newly developed protocol reduces the number of waste products formed in the synthetic transformation. A structure–reactivity relationship study of numerous [hydroxy(tosyloxy)iodo]arenes toward haloalkenes is reported. The results highlight the challenge of obtaining a chemoselective reaction using these reagents.

Catalytic Hydrolysis of Adenosine 2‘,3‘-Cyclic Monophosphate by CuIITerpyridine

1999 ◽  
Vol 38 (13) ◽  
pp. 3215-3222 ◽  
Author(s):  
Lisa A. Jenkins ◽  
James K. Bashkin ◽  
Jennifer D. Pennock ◽  
Jan Florián ◽  
Arieh Warshel
Keyword(s):  
Catalytic Hydrolysis ◽  
Cyclic Monophosphate ◽  
Hydrolysis Of

scholarly journals Hydrolysis of Uridine 2',3'-Cyclic Monophosphate and Uridylyl-3',5'-uridine Promoted by Bimetallic Cu2+ and Zn2+ Complexes of BISDIEN.

1999 ◽  
Vol 53 ◽  
pp. 453-456 ◽  
Author(s):  
Satu Mikkola ◽  
Qi Wang ◽  
Zoltan Jori ◽  
Mia Helkearo ◽  
Harri Lönnberg ◽  
...  
Keyword(s):  
Cyclic Monophosphate ◽  
Hydrolysis Of

scholarly journals Conversion of 1-[((S)-2-hydroxy-2-oxo-1,4,2-dioxaphosphorinan-5-yl)methyl]cytosine to cidofovir by an intracellular cyclic CMP phosphodiesterase.

1997 ◽  
Vol 41 (3) ◽  
pp. 641-646 ◽  
Author(s):  
D B Mendel ◽  
T Cihlar ◽  
K Moon ◽  
M S Chen
Keyword(s):  
Parent Compound ◽  
Catalytic Efficiency ◽  
Cyclic Monophosphate ◽  
Nucleotide Analog ◽  
Target Organs ◽  
Hcmv Disease ◽  
Methyl Cytosine ◽  
Reduced Toxicity ◽  
Hydrolysis Of ◽  
Cyclic Cmp

Cidofovir (HPMPC) [1-[(S)-3-hydroxy-2-(phosphonomethoxy)propyl]-cytosine] is an acyclic nucleotide analog with potent and selective activity against herpesviruses. The prodrug, cyclic HPMPC (cHPMPC) [1-[((S)-2-hydroxy-2-oxo-1,4,2-dioxaphosphorinan-5-yl) methyl]cytosine], has antiviral activity similar to that of the parent compound but exhibits reduced toxicity in animal models. cHPMPC is converted to cidofovir by a cellular cyclic CMP phosphodiesterase (EC 3.1.4.37) which hydrolyzes a variety of substrates, including adenosine 3',5'-cyclic monophosphate (cAMP) and cytidine 3',5'-cyclic monophosphate (cCMP). The K(m) and Vmax values for hydrolysis of cHPMPC by cCMP phosphodiesterase purified from human liver are 250 microM and 0.66 nmol.min-1.unit-1, respectively. These values are similar to the K(m) and Vmax values for cAMP (23 microM and 1.16 nmol.min-1.unit-1, respectively) and cCMP (75 microM and 2.32 nmol.min-1.unit of enzyme-1, respectively). The catalytic efficiency (Vmax/K(m) ratio) of this enzyme for the cHPMPC substrate is only 10- to 20-fold lower than those for the natural cyclic nucleotides, indicating that cHPMPC is a viable intracellular substrate for the human enzyme. Kinetic analysis indicates that cHPMPC, cAMP, and cCMP are competitive with respect to each other and that they are hydrolyzed by the same enzyme. cHPMPC is hydrolyzed to cidofovir in all primary human cell systems tested, including those derived from target organs that might be infected in patients with human cytomegalovirus (HCMV) disease. Importantly, hydrolysis of cHPMPC is not diminished in cells infected with HCMV.

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