A General, Modular Approach to a New Family of Amine-Substituted Arylboronic Acid Saccharide Chemosensors

Bryan M. Schertzer; Sheila N. Baker; Steven T. Diver; Gary A. Baker

doi:10.1071/CH05292

RESEARCH ARTICLE

Previous Next Contents Vol 59(9)

A General, Modular Approach to a New Family of Amine-Substituted Arylboronic Acid Saccharide Chemosensors

Bryan M. Schertzer ^A , Sheila N. Baker ^B , Steven T. Diver ^A ^D and Gary A. Baker ^C ^D

+ Author Affiliations

- Author Affiliations

^A Department of Chemistry, University at Buffalo, State University of New York, Buffalo, NY 14260, USA.

^B Ionnovations, 704 Gracewood Way, Knoxville, TN 37934, USA.

^C Chemical Sciences Division, Oak Ridge National Laboratory, Oak Ridge, TN 37831-6110, USA.

^D Corresponding authors. Email: diver@nsm.buffalo.edu; bakerga1@ornl.gov

Australian Journal of Chemistry 59(9) 633-639 https://doi.org/10.1071/CH05292
Submitted: 31 October 2005 Accepted: 15 August 2006 Published: 19 October 2006

Abstract

A general synthetic approach towards a class of water-soluble, high quantum yield fluorescent saccharide reporters using 6-morpholinonaphthalene-2-yl boronic acid as an illustrative case is reported. The strength and flexibility of this approach, which utilizes the Buchwald–Hartwig cross-coupling reaction, is further underscored by the preparation of several additional aminonaphthalenes in excellent yield, including one that bears a chiral unit.

Acknowledgements

We gratefully acknowledge support of this work through ORNL (Wigner Fellowship to G.A.B.) and the NSF (Career CHE-0092434 to S.T.D.). We thank the referees whose insightful comments and suggestions helped us to markedly improve upon the manuscript.

References

^A As pointed out by one of the referees, during the preparation on the manuscript of this paper, a report disclosing a boronic acid-based saccharide probe with a structure similar to 7 appeared from the Wang group.^[^14a^] Our method offers advantages both in terms of synthetic efficiency and flexibility. The Buchwald–Hartwig amination reported here will be useful for the convergent construction of sugar chemosensors from aromatic moieties and complex amines, not possible by existing methods, even for structurally similar naphthyl amines. In a recent follow-up publication, the same group reported a four-step synthesis of 5-(dimethylamino)naphthalene-1-boronic acid with an overall yield of ca. 27%.^[^14b^]

A General, Modular Approach to a New Family of Amine-Substituted Arylboronic Acid Saccharide Chemosensors

Abstract

Acknowledgements

Subscriber Login