Bifunctional Synthetic Enzymes via Alternating Copolymerization. I. Copolymers Containing Alternating Imidazole and Hydroxamic Functions

Vanderbilt, David P.; Butler, George B.

doi:10.1080/00222338508056618

Cited by 2 publications

(1 citation statement)

References 39 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Cyclic N-hydroxyimides are versatile compounds which are widely used in peptide synthesis [1], aerobic oxidation [2][3][4], and polymerization [5,6]. Particularly, N-hydroxysuccinimide (NHS, Fig.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of N-hydroxysuccinimide from succinic acid and hydroxylammonium chloride using Amberlyst A21 as reusable solid base catalyst

Le¹,

Nishimura²,

Ebitani³

2018

AIP Conference Proceedings

View full text Add to dashboard Cite

Abstract. Solid base catalysts were studied for the first time to synthesize N-hydroxysuccinimide (NHS) through the reaction of succinic acid with hydroxylammonium chloride. The highest yield of 42% (±3%) with 65% (±4%) selectivity toward NHS production was achieved by using Amberlyst A21, which is a weak base anion-exchange resin. The present catalyst could be recycled during five runs without significant decreases in activity. Also, efficacy for the Amberlyst A21 mediated reaction was also explored with other dicarboxylic acids such as phthalic acid, glutaric acid, and maleic acid.

show abstract

Section: Introductionmentioning

confidence: 99%

Synthesis of N-hydroxysuccinimide from succinic acid and hydroxylammonium chloride using Amberlyst A21 as reusable solid base catalyst

Le¹,

Nishimura²,

Ebitani³

2018

AIP Conference Proceedings

View full text Add to dashboard Cite

show abstract

Catalysis of esterolytic reactions by water-soluble imidazole containing polymers

Overberger¹,

Mitra²

1979

Pure and Applied Chemistry

View full text Add to dashboard Cite

In a review article [Accounts Chem. Res., 2, 217 (1969')] is a Summation of our work up to 1968. In this review we summarized the activity of polyvinylfmfdazole and copolymers in esterolytic reactions. We explained the increased reactivity of these polymeric reactants in terms of cc;>operative effects and electrostatic factors. In 1967, we blundered into the extremely interesting discovery that long~chain esters provided us with enormaus acceleration of rates at room temperature and we have attributed this in "general" terminology to apolar bonding as a third factqr to understand the high reactivity of these synthetic macromolecules. Reference 1 describes our recent published werk. We are heavily emphasizing the apolar bonding concept. Related work.which conceptually can be regarded as simflar to our own discovery was carried out by the group of Professor Irving M. Klotz at Northwestern(2}, the group of Professor Kabanov at the University of Moscow(3}, and the group of Professor Kunitake(4}. This lecture will briefly review the background of the prob1em and discuss ·in detail the catalysis of esterolytic reactions by water-soluble copolymers of vinylimidazoles and vinylamines. Synthetic macromolecules containing pendant imidazole groups have been used as catalysts for the hydrolysis of esters. This report extends that study to copolymers of 4(5}-vfnylimidazole and vinylamine. The latter component renders these polymers water soluble and, therefore, their catalytic activity could be studied in a totally aqueous environment. The precursor for the vinylamine monomer used for these copolymerizations was N-vinyl-t-butylcarbamate which, in turn, was prepared from vinylfsocyanate. Extremely large rate enhancements were observed with these catalysts for hydrolyses of activated esters and these were attributed to cooperative, electrostatic and hydrophobic effects. The large cooperative effects were due to tight coiling of these copolymers in water, increasing the proximity of imidazole groups for interaction. The highly aqueous media in which these esterolysis could be carried out with these copolymers resulted in very large hydrophobic effects with long chain ester substrates. Less aqueous environments led to dramatic rate decreases. Esterolytic studies were also carried out under conditions of excess substrate which showed typical steady-state kinetics from which rates of deacylation of the catalyst could be determined. The fraction of imidazoles in these copolymers that were acylated under steady-state conditions.were qufte low.

show abstract

Bifunctional Synthetic Enzymes via Alternating Copolymerization. I. Copolymers Containing Alternating Imidazole and Hydroxamic Functions

Cited by 2 publications

References 39 publications

Synthesis of N-hydroxysuccinimide from succinic acid and hydroxylammonium chloride using Amberlyst A21 as reusable solid base catalyst

Synthesis of N-hydroxysuccinimide from succinic acid and hydroxylammonium chloride using Amberlyst A21 as reusable solid base catalyst

Catalysis of esterolytic reactions by water-soluble imidazole containing polymers

Contact Info

Product

Resources

About