Boronic Groups Research Articles

Adenosine 3',5'-phosphate phosphodiesterase and pheromone response in the yeast Saccharomyces cerevisiae.

Theophylline, aminophylline, and isobutylmethylxanthine, compounds reported to be inhibitors of adenosine 3',5'-phosphate (cAMP) phosphodiesterase, prevented the alpha-factor-induced cell cycle arrest of Saccharomyces cerevisiae a cells. To determine whether the in vivo effect of these methylxanthines on yeast pheromone response was related to their known biochemical mode of action, two assays for cAMP phosphodiesterase based on affinity of the product of the reaction (5'-AMP) for boronate groups were developed and were used to monitor the activity of the low Km cAMP phosphodiesterase present in yeast extracts. It was found that the relative efficacy of the methylxanthines as inhibitors of this enzyme in vitro was correlated with the degree to which they antagonized alpha-factor action in vivo. These results were consistent with our previous proposal that pheromone action involves a lowering of cAMP level in the target cell.

The synthesis and complex forming properties of copolymers of N-vinylpyrrolidone with aminoalkyl methacrylates, containing boronate groups

Water soluble polymers containing boronate groups have been synthesized by alkylation of copolymers of vinylpyrrolidone and aminoalkyl methacrylates with p -bromotolylboroxole. With adenosine taken as an example, the complex forming properties of the resulting polymers in relation to cis -diols have been studied.

A bromomethanetriboronic ester

Tetrakis(dimethoxyboryl)methane, C[B(OMe) 2] 4, reacts with pinacol to form the corresponding pinacol boronic ester, C(BO 2C 2Me 4) 4, which on treatment with alkyllithium yields the corresponding triborylmethide anion, −C(BO 2C 2Me 4) 3, which with bromine gives the bromomethanetriboronic ester, BrC(BO 2C 2Me 4) 3. Alkyllithium abstracts a boronic ester group from the bromomethanetriboronic ester to form the carbanion, −CBr(BO 2C 2Me 4) 2, which has been brominated to yield the dibromomethanediboronic ester, Br 2C(BO 2C 2Me 4) 2, and has also been treated with triphenyltin chloride to form the tin derivative, Ph 3SnCBr(BO 2C 2Me 4) 2. Sodium acetate converts the dibromomethanediboronic ester to the diacetate, (AcO) 2C(BO 2C 2Me 4) 2, but the bromomethanetriboronic ester appeared to be inert toward nucleophilic displacement reactions. The bromomethanediboronic ester BrCH(BO 2C 2Me 4) 2 has also been made.

Boronic ester neighboring groups

Boronic ester neighboring groups

Arylboronic acids. Medium-size ring-containing boronic ester groups

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTArylboronic acids. Medium-size ring-containing boronic ester groupsWilliam M. Cummings, Clifford H. Cox, and H. R. SnyderCite this: J. Org. Chem. 1969, 34, 6, 1669–1674Publication Date (Print):June 1, 1969Publication History Published online1 May 2002Published inissue 1 June 1969https://doi.org/10.1021/jo01258a029RIGHTS & PERMISSIONSArticle Views319Altmetric-Citations14LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (764 KB) Get e-Alerts Get e-Alerts