Document Detail

Stereochemical course of the reaction catalyzed by the cyclic GMP phosphodiesterase from retinal rod outer segments.
MedLine Citation:
PMID:  2844755     Owner:  NLM     Status:  MEDLINE    
The stereochemical course of hydrolysis catalyzed by the cyclic GMP phosphodiesterase from bovine retinal rod outer segments was determined. The Sp diastereomer of guanosine 3',5'-cyclic monophosphorothioate was hydrolyzed by cyclic GMP phosphodiesterase in H2(18)O to give [16O,18O]guanosine 5'-monophosphorothioate. This isotopomer was reacted with diphenyl phosphorochloridate to form the two diastereomers of P1-(5'-guanosyl) P2-(diphenyl) 1-thiodiphosphate. The 31P NMR spectrum of this mixture of diastereomers was identical to that obtained from [16O,18O]guanosine 5'-monophosphorothioate resulting from the hydrolysis of the Rp diastereomer of guanosine 5'-p-nitrophenyl phosphorothioate by snake venom phosphodiesterase. This finding indicates that the 18O is bridging in the Rp diastereomer of the P1-(5'-guanosyl) P2-(diphenyl) 1-thiodiphosphate and nonbridging in the Sp diastereomer. As the snake venom phosphodiesterase reaction is known to proceed with retention of configuration, it follows that hydrolysis by retinal rod cyclic GMP phosphodiesterase proceeds with inversion of configuration at the phosphorus atom.
F Eckstein; J W Karpen; J M Critchfield; L Stryer
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  The Journal of biological chemistry     Volume:  263     ISSN:  0021-9258     ISO Abbreviation:  J. Biol. Chem.     Publication Date:  1988 Oct 
Date Detail:
Created Date:  1988-11-07     Completed Date:  1988-11-07     Revised Date:  2008-11-21    
Medline Journal Info:
Nlm Unique ID:  2985121R     Medline TA:  J Biol Chem     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  14080-5     Citation Subset:  IM    
Max-Planck-Institut für Experimentelle Medizin, Abteilung Chemie, Gottingen, Federal Republic of Germany.
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MeSH Terms
3',5'-Cyclic-GMP Phosphodiesterases / metabolism*
Cyclic GMP / analogs & derivatives*,  metabolism
Magnetic Resonance Spectroscopy
Photoreceptor Cells / enzymology*
Rod Cell Outer Segment / enzymology*
Substrate Specificity
Thionucleotides / metabolism*
Grant Support
Reg. No./Substance:
0/Thionucleotides; 67736-26-9/guanosine-3',5'-cyclic phosphorothioate; 7665-99-8/Cyclic GMP; EC',5'-Cyclic-GMP Phosphodiesterases

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