Saccharide sensing with molecular receptors based on boronic acid

Tony D. James, K. R.A. Samankumara Sandanayake, Seiji Shinkai

Research output: Contribution to journalArticle

667 Citations (Scopus)

Abstract

The lock-and-key principle of natural systems is based on complex interactions like hydrogen bonding. Many synthetic systems that attempt to mimic natural systems have also used hydrogen bonding as the main binding force and have met with great success in non-hydrogen-bonding solvents that do not compete with the guest for the binding pocket. In contrast, natural systems function in water, a very competitive solvent. Synthetic hydrogen-bonding systems may yet evolve to be successful in water. If this transition can not be made, synthetic answers can nevertheless take inspiration from nature without slavishly following the blue print. This is not an attempt to re-invent the "lock": a new locking mechanism merely replaces the existing one. The inspiration might be the view of the hydrogen bond as an easily reversible "covalent" bond. Screening the literature we rediscovered boronic acids, which have been known for over 100 years. Conveniently, boronic acids rapidly and reversibly form cyclic esters with diols in basic aqueous media. Saccharides and other related "keys" contain a contiguous array of cyclic alcohols. In this work we hope to demonstrate that saccharide "keys" and boronic acid "locks" can open the door to a new and exciting field of research.

Original languageEnglish
Pages (from-to)1910-1922
Number of pages13
JournalAngewandte Chemie (International Edition in English)
Volume35
Issue number17
DOIs
Publication statusPublished - Jan 1 1996

Fingerprint

Boronic Acids
Hydrogen bonds
Acids
Covalent bonds
Water
Esters
Screening
Alcohols

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Cite this

Saccharide sensing with molecular receptors based on boronic acid. / James, Tony D.; Samankumara Sandanayake, K. R.A.; Shinkai, Seiji.

In: Angewandte Chemie (International Edition in English), Vol. 35, No. 17, 01.01.1996, p. 1910-1922.

Research output: Contribution to journalArticle

James, Tony D. ; Samankumara Sandanayake, K. R.A. ; Shinkai, Seiji. / Saccharide sensing with molecular receptors based on boronic acid. In: Angewandte Chemie (International Edition in English). 1996 ; Vol. 35, No. 17. pp. 1910-1922.
@article{4c1e88f2d3c448c7923457e60f226282,
title = "Saccharide sensing with molecular receptors based on boronic acid",
abstract = "The lock-and-key principle of natural systems is based on complex interactions like hydrogen bonding. Many synthetic systems that attempt to mimic natural systems have also used hydrogen bonding as the main binding force and have met with great success in non-hydrogen-bonding solvents that do not compete with the guest for the binding pocket. In contrast, natural systems function in water, a very competitive solvent. Synthetic hydrogen-bonding systems may yet evolve to be successful in water. If this transition can not be made, synthetic answers can nevertheless take inspiration from nature without slavishly following the blue print. This is not an attempt to re-invent the {"}lock{"}: a new locking mechanism merely replaces the existing one. The inspiration might be the view of the hydrogen bond as an easily reversible {"}covalent{"} bond. Screening the literature we rediscovered boronic acids, which have been known for over 100 years. Conveniently, boronic acids rapidly and reversibly form cyclic esters with diols in basic aqueous media. Saccharides and other related {"}keys{"} contain a contiguous array of cyclic alcohols. In this work we hope to demonstrate that saccharide {"}keys{"} and boronic acid {"}locks{"} can open the door to a new and exciting field of research.",
author = "James, {Tony D.} and {Samankumara Sandanayake}, {K. R.A.} and Seiji Shinkai",
year = "1996",
month = "1",
day = "1",
doi = "10.1002/anie.199619101",
language = "English",
volume = "35",
pages = "1910--1922",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
publisher = "John Wiley and Sons Ltd",
number = "17",

}

TY - JOUR

T1 - Saccharide sensing with molecular receptors based on boronic acid

AU - James, Tony D.

AU - Samankumara Sandanayake, K. R.A.

AU - Shinkai, Seiji

PY - 1996/1/1

Y1 - 1996/1/1

N2 - The lock-and-key principle of natural systems is based on complex interactions like hydrogen bonding. Many synthetic systems that attempt to mimic natural systems have also used hydrogen bonding as the main binding force and have met with great success in non-hydrogen-bonding solvents that do not compete with the guest for the binding pocket. In contrast, natural systems function in water, a very competitive solvent. Synthetic hydrogen-bonding systems may yet evolve to be successful in water. If this transition can not be made, synthetic answers can nevertheless take inspiration from nature without slavishly following the blue print. This is not an attempt to re-invent the "lock": a new locking mechanism merely replaces the existing one. The inspiration might be the view of the hydrogen bond as an easily reversible "covalent" bond. Screening the literature we rediscovered boronic acids, which have been known for over 100 years. Conveniently, boronic acids rapidly and reversibly form cyclic esters with diols in basic aqueous media. Saccharides and other related "keys" contain a contiguous array of cyclic alcohols. In this work we hope to demonstrate that saccharide "keys" and boronic acid "locks" can open the door to a new and exciting field of research.

AB - The lock-and-key principle of natural systems is based on complex interactions like hydrogen bonding. Many synthetic systems that attempt to mimic natural systems have also used hydrogen bonding as the main binding force and have met with great success in non-hydrogen-bonding solvents that do not compete with the guest for the binding pocket. In contrast, natural systems function in water, a very competitive solvent. Synthetic hydrogen-bonding systems may yet evolve to be successful in water. If this transition can not be made, synthetic answers can nevertheless take inspiration from nature without slavishly following the blue print. This is not an attempt to re-invent the "lock": a new locking mechanism merely replaces the existing one. The inspiration might be the view of the hydrogen bond as an easily reversible "covalent" bond. Screening the literature we rediscovered boronic acids, which have been known for over 100 years. Conveniently, boronic acids rapidly and reversibly form cyclic esters with diols in basic aqueous media. Saccharides and other related "keys" contain a contiguous array of cyclic alcohols. In this work we hope to demonstrate that saccharide "keys" and boronic acid "locks" can open the door to a new and exciting field of research.

UR - http://www.scopus.com/inward/record.url?scp=0029902912&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0029902912&partnerID=8YFLogxK

U2 - 10.1002/anie.199619101

DO - 10.1002/anie.199619101

M3 - Article

AN - SCOPUS:0029902912

VL - 35

SP - 1910

EP - 1922

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 17

ER -