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Synthesis of Boron‐Containing ADP and GDP Analogues: Nucleoside 5′‐( P α ‐Boranodiphosphates)
Author(s) -
Lin Jinlai,
He Kaizhang,
Ramsay Shaw Barbara
Publication year - 2000
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(20000705)83:7<1392::aid-hlca1392>3.0.co;2-h
Subject(s) - chemistry , nucleoside , lipophilicity , guanosine , diastereomer , adenosine , stereochemistry , medicinal chemistry , biochemistry
New 5′‐( P α ‐boronated) analogues of the naturally occurring nucleoside diphosphates ADP and GDP were synthesized in good yields, i.e. , adenosine 5′‐( P α ‐boranodiphosphate) (ADP α B; 5a ) and guanosine 5′‐( P α ‐boranodiphosphate) (GDP α B; 5b ). Their diastereoisomers were successfully separated by reversed‐phase HPLC, and chemical structures were established via spectroscopic methods. The isoelectronic substitution of borane (BH 3 ) for one of the non‐bridging O‐atoms in phosphate diesters should impart an increase in lipophilicity and change in polarity in ADP α B and GDP α B. The boronated nucleoside diphosphates could be employed for investigations of the stereochemical course and metal requirements of enzymatic reactions involving ADP and GDP, and as carriers of 10 B in boron neutron‐capture therapy (BNCT) for the treatment of cancer.