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Biocompatible Conjugation of Tris Base to 2-acetyl and 2-formyl Phenylboronic Acid

Biocompatible Conjugation of Tris Base to 2-acetyl and 2-formyl Phenylboronic Acid

Kaicheng Li, Michael A Kelly, Jianmin Gao

Org Biomol Chem. 2019 Jun 28;17(24):5908-5912.

PMID: 31145403

Abstract:

We describe the biocompatible conjugation of the Tris base to 2-formyl and 2-acetylphenylboronic acid (abbreviated as 2-FPBA and 2-APBA respectively), which have emerged as a versatile chemotype for fast biocompatible conjugation reactions. Tris base was found to react with 2-FPBA/APBA to give oxazolidinoboronate (OzB) complexes, analogous to the thiazolidinoboronate (TzB) and imidazolidinoboronate (IzB) complex formation that we recently reported. The Tris conjugations proceed well in complex biological media, and in contrast to the TzB/IzB complexes, the Tris conjugates exhibit superior kinetic stability (dissociation over days) as well as chemical stability against oxidation. We demonstrate the utility of such conjugation chemistries via a small molecule-induced peptide cyclization in blood serum.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP308103404	2-Acetylphenylboronic acid		308103-40-4	Price
LS793645	(4-benzyloxy-2-formyl)phenylboronic acid			Price

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