Controlling rates and reversibilities of elimination reactions of hydroxybenzylammoniums by tuning dearomatization energies-Reference-Cited by-同舟云学术

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Controlling rates and reversibilities of elimination reactions of hydroxybenzylammoniums by tuning dearomatization energies

Published:2024 Issue:27 Volume:15 Page:10448-10454
ISSN:2041-6520
Container-title:Chemical Science
language:en
Short-container-title:Chem. Sci.

Author:

Fu Zihuan¹^ORCID,Treacy Joseph W.¹^ORCID,Hosier Brock M.¹,Houk K. N.¹^ORCID,Maynard Heather D.¹^ORCID

Affiliation:

1. Department of Chemistry and Biochemistry, California NanoSystems Institute, University of California, Los Angeles, California, 90095-1569, USA

Abstract

The factors that govern hydroxybenzylammonium-mediated amine releasing reactions have been computationally examined. This mechanistic insight led to subsequent experimental validation and generation of release half-lives as fast as 18 minutes.

Funder

National Science Foundation

Foundation for the National Institutes of Health

Publisher

Royal Society of Chemistry (RSC)

Link

http://pubs.rsc.org/en/content/articlepdf/2024/SC/D4SC02985B

Reference36 articles.

1. Reversible PEGylation: A Novel Technology To Release Native Interferon α2 over a Prolonged Time Period

2. The azaquinone-methide elimination: comparison study of 1,6- and 1,4-eliminations under physiological conditions

3. Drug Delivery Systems Employing 1,6-Elimination: Releasable Poly(ethylene glycol) Conjugates of Proteins

4. Cathepsin B-sensitive dipeptide prodrugs. 1. A model study of structural requirements for efficient release of doxorubicin

5. Cathepsin B-sensitive dipeptide prodrugs. 2. Models of anticancer drugs paclitaxel (Taxol®), mitomycin C and doxorubicin

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