Boronolectins and fluorescent boronolectins: An examination of the detailed chemistry issues important for the design

Yan, Jun; Fang, Hao; Wang, Binghe

doi:10.1002/med.20038

Cited by 177 publications

(174 citation statements)

References 114 publications

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“…[52][53][54][55] By combining the boronic acid moiety that binds selectively to a particular carbohydrate with a sensitive analytical technique, such as fluorescence, photoinduced electron transfer, colorimetry or electrochemistry, it has become possible to develop a large variety of highly sensitive sensors for the detection and quantification of glucose and other carbohydrates. Given the importance of glucose monitoring for patients with diabetes and for other applications, a great amount of effort has been directed towards the development of boronic acid-containing sensors that can operate under physiological conditions for routine monitoring.…”

Section: Molecular Receptors and Sensorsmentioning

confidence: 99%

Expanding Roles for Organoboron Compounds – Versatile and Valuable Molecules for Synthetic, Biological and Medicinal Chemistry

Petasis

2007

Aust. J. Chem.

109

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The present essay offers an overview of the latest developments in the chemistry of organoboron compounds. The unique structural characteristics and the versatile reactivity profile of organoboron compounds continue to expand their roles in several areas of chemistry. A growing number of boron-mediated reactions have become vital tools for synthetic chemistry, particularly in asymmetric synthesis, metal-catalyzed processes, acid catalysis, and multicomponent reactions. As a result, boronic acids and related molecules have now evolved as major players in synthetic and medicinal chemistry. Moreover, their remnant electrophilic reactivity, even under physiological conditions, has allowed their incorporation in a growing number of bioactive molecules, including bortezomib, a clinically approved anticancer agent. Finally, the sensitive and selective binding of boronic acids to diols and carbohydrates has led to the development of a growing number of novel chemosensors for the detection, quantification, and imaging of glucose and other carbohydrates. There is no doubt that the chemistry of organoboron compounds will continue to expand into new discoveries and new applications in several fields of science. Long History -Expanding RolesOrganic compounds containing boron have been known for over a century, and many aspects of their chemical properties and reactivity have been known for quite some time. Since the discovery and development of hydroboration, the resulting organoboranes are among the most widely used reagents and intermediates in organic synthesis including asymmetric reactions. Also, early investigations on the chemistry of boron hydrides and carboranes revealed new classes of compounds with unique structure and reactivity that continue to attract attention. Despite these early discoveries, however, the real potential of some of the more versatile and chemically stable organoboron compounds was not realized until recently.Indeed, the growing list of valuable organoboron compounds in addition to organoboranes [1] now includes organoboronic acids and boronates, [2] and more recently organotrifluoroborates.

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Section: Molecular Receptors and Sensorsmentioning

confidence: 99%

Expanding Roles for Organoboron Compounds – Versatile and Valuable Molecules for Synthetic, Biological and Medicinal Chemistry

Petasis

2007

Aust. J. Chem.

109

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“…[1] In addition, attention has recently also been paid to their applications in molecular recognition and pharmaceutical candidates owing to their high stability and low toxicity. [2] Their increasing importance has been justified in the development of new, mild and efficient methods to provide access to a large pool. Of particular interest is the synthesis of arylboronic acids and their esters substituted with a wide range of functional groups.…”

Section: Introductionmentioning

confidence: 99%

Cyclopalladated Ferrocenylimine as Efficient Catalyst for the Syntheses of Arylboronate Esters

Wang

Li²,

Cui

et al. 2010

Adv Synth Catal

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The cyclopalladated ferrocenylimine I and its phosphine adducts IIa-f were prepared and evaluated in the borylation of aryl halides. The tricyclohexylphosphine adduct IIb exhibited highly catalytic activity for the coupling of aryl and heteroaryl bromides containing various functional groups with low catalyst loading (2 mol%). Aryl and heteroaryl chlorides were smoothly converted into the corresponding boronates in the presence of the monophosphinobiaryl ligand (XPhos) adduct IIf. It was proposed that palladacycle was only a reservoir of the catalytically active species from the investigation on the reaction mechanism.

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“…In contrast, the latter group of CBMs relies solely on non-covalent interactions, such as hydrogen bond, CH/π interaction, and metal coordination, for binding to carbohydrates. Although the boronic acid-dependent CBMs have been extensively studied, as exemplified by "boronolectins" (14), this minireview focuses on the more biomimetic CBMs and discusses recent design principles of boronic acid-independent CBMs. We also highlight a unique class of naturally-occurring CBMs, pradimicins (PRMs) and its congeners (15), and describe the molecular basis of their carbohydrate recognition.…”

Section: A Introductionmentioning

confidence: 99%

Carbohydrate-Binding Molecules with Non-Peptidic Skeletons

Nakagawa

Ito

2012

TIGG

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Emerging biological significance of carbohydrates has increased the importance of carbohydrate-binding molecules (CBMs) as diagnostic and therapeutic agents as well as research tools in glycobiology. Especially, there are rapidly growing interests in small molecules with a carbohydratebinding property due to the ease of preparation and chemical modification. This minireview focuses on small-size CBMs that bind carbohydrates through non-covalent interactions. Small-size CBMs of synthetic origin have been progressively developed in the field of supramolecular chemistry. The representative architectures of the synthetic CBMs are briefly reviewed mainly focusing on recent examples. We also highlight naturally-occurring CBMs, pradimicins and its congeners. They are the only class of natural products with a lectin-like ability to recognize D-mannosides (Man) in the presence of Ca 2+ ion. Our recent findings on molecular basis of their Man recognition are also described.

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Boronolectins and fluorescent boronolectins: An examination of the detailed chemistry issues important for the design

Cited by 177 publications

References 114 publications

Expanding Roles for Organoboron Compounds – Versatile and Valuable Molecules for Synthetic, Biological and Medicinal Chemistry

Expanding Roles for Organoboron Compounds – Versatile and Valuable Molecules for Synthetic, Biological and Medicinal Chemistry

Cyclopalladated Ferrocenylimine as Efficient Catalyst for the Syntheses of Arylboronate Esters

Carbohydrate-Binding Molecules with Non-Peptidic Skeletons

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