Document Detail

Use of phosphoimidazolide-activated guanosine to investigate the nucleophilicity of spermine and spermidine.
MedLine Citation:
PMID:  11543598     Owner:  NASA     Status:  MEDLINE    
Guanosine 5'-phosphate 2-methylimidazolide (2-MeImpG), a labile phosphoimidazolide analog of guanosine triphosphate, was used to test the reactivity of the natural polyamines (PAs), spermine (spm) and spermidine (spd). The products are the guanosine 5'-phosphate-polyamine derivatives (PA-pG: spd-pG and spm-pG) which are quite stable in the range 4 < pH < 11. Our study is the first of which we are aware that reports on the nucleophilicity of these amines. The main findings are as follows. (i) HPLC analysis of the products indicates the formation of only two of the three possible spd products and only one of the two possible spm products. These results can be explained if only the primary amino groups of the two polyamines are reactive, while the secondary amino groups are rendered unreactive by a steric effect. The reactions of 2-MeImpG and other phosphoimidazolide derivatives of nucleosides (ImpNs) with primary and secondary monoamines support this interpretation (Kanavarioti et al. J. Org. Chem. 1995, 60, 632). (ii) The product ratio of the two spd-pG adducts derived from the primary amino groups varies between 2.40 and 0.71 in the range 6.1 < or equal to pH < or equal to 11.9. Such small variation in the product ratio can only be rationalized by the similar, but not identical, basicity of the two primary amino groups and provides strong support for a previously reported model for polyamine ionization (Onasch et. al. Biophys. Chem. 1984, 19, 245). (iii) On the basis of our kinetic determinations conditions at which the nucleophilicity of these amines is at a minimum and at which other interactions with ImpNs could be tested can be chosen.
A Kanavarioti; E E Baird; P J Smith
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Publication Detail:
Type:  Journal Article; Research Support, U.S. Gov't, Non-P.H.S.    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  60     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  1995  
Date Detail:
Created Date:  1997-09-14     Completed Date:  1997-09-14     Revised Date:  2007-08-01    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  4873-83     Citation Subset:  S    
Department of Chemistry and Biochemistry, University of California, Santa Cruz 95064, USA.
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MeSH Terms
5'-Guanylic Acid / analogs & derivatives*,  chemistry
Chromatography, High Pressure Liquid
Hydrogen-Ion Concentration
Magnetic Resonance Spectroscopy
Osmolar Concentration
Spermidine / analogs & derivatives,  chemistry*
Spermine / analogs & derivatives,  chemistry*
Reg. No./Substance:
0/Protons; 124-20-9/Spermidine; 71-44-3/Spermine; 80242-42-8/guanosine 5'-phospho-2-methylimidazolide; 85-32-5/5'-Guanylic Acid
A Kanavarioti / U CA, Santa Cruz

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