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An Efficient Methodology to Introduce

An Efficient Methodology to Introduce

Erik T Hernandez, Igor V Kolesnichenko, James F Reuther, Eric V Anslyn

New J Chem. 2017 Jan 7;41(1):126-133.

PMID: 28649175

Abstract:

Current approaches for incorporating boronic acids into peptides require one of the following: the synthesis of commercially unavailable pinacol-protected boronate ester amino acid building blocks, amidation of small-molecule amine-containing boronic acids, or reductive amination of amine residues with 2-formylphenyl boronic acid. These methods have drawbacks, such as the use of excess starting materials, the lack of reactive-site specificity, or the inability to add multiple boronic acids in solution. In addition, several of these approaches do not allow for incorporation of the critical o-aminomethyl functionality that allows for binding of sacharrides under physiological conditions. In this work, we report three methods to functionalize synthetic peptides with boronic acids using solid-phase and solution-phase chemistries by alkylating a secondary amine with o-(bromomethyl)phenylboronic acid. Solution-phase chemistries afforded the highest yields, and were used to synthesize seven complex biotinylated multi-boronic acid peptides.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP91983141	2-(Bromomethyl)phenylboronic acid		91983-14-1	Price

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