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Switching the Chemoselectivity in the Preparation of [F]FNA--CooP, a Free Thiol-Containing Peptide for Targeted Positron Emission Tomography Imaging of Fatty Acid Binding Protein 3.
Mol Pharm
August 2024
Turku PET Centre, University of Turku, Kiinamyllynkatu 4-8, Turku FI-20520, Finland.
Fatty acid binding protein 3 (FABP3) is expressed both in tumor cells and in the tumor vasculature, making it a potential target for medical imaging and therapy. In this study, we aimed to radiolabel a CooP peptide with a free amino and thiol group, and evaluate the radiolabeled product [F]FNA--CooP for imaging FABP3 expression in breast cancer brain metastases by positron emission tomography. [F]FNA--CooP was prepared by highly chemoselective -acylation and characterized using different chemical approaches.
View Article and Find Full Text PDFA concise chemoenzymatic total synthesis of neutral Globo-series glycosphingolipids Globo A and Globo B, and Forssman and para-Forssman antigens.
Glycoconj J
October 2023
Department of Chemistry, National Tsing Hua University, 101 Section 2, Kuang Fu Road, Hsinchu, 30013, Taiwan.
Globo A is a neutral Globo-series glycosphingolipid (GSL) that shows natural properties of a cytotoxicity receptor NKp44 binding ligand. The highly complex heptasaccharide glycan structure of Globo A combined with its biological profile provides a unique target for the development of a synthetic method to facilitate its bioactivity studies. Here, a concise chemoenzymatic route to the synthesis of Globo A and its α1,3-galactose-linked congener Globo B is reported.
View Article and Find Full Text PDFChemoselective N-Acylation of Amines with Acylsilanes under Aqueous Acidic Conditions.
Org Lett
August 2023
School of Pharmaceutical Science and Technology (SPST), Tianjin University, Tianjin 300072, P.R. China.
We report a facile method for forming amide bonds between acylsilanes and a wide range of amines in the presence of a mild chlorinating agent under aqueous acidic conditions. The reaction is highly chemoselective, as exemplified by the late-stage modification of a panel of approved drugs and natural products containing reactive functionalities.
View Article and Find Full Text PDFChemoselective Lipase-Catalyzed Synthesis of Amido Derivatives from 5-Hydroxymethylfurfurylamine.
ACS Sustain Chem Eng
July 2023
Organic and Inorganic Chemistry Department, University of Oviedo, Avenida Julián Clavería 8, Oviedo 33006, Spain.
The acylations of furfurylamine and 5-hydroxymethylfurfurylamine (HMFA) have been studied finding immobilized lipase B (CALB) as an ideal biocatalyst. CALB was used immobilized on two different supports (Novozyme 435 and EziG-CALB), with the polymer-coated controlled porosity glass carrier material from EnginZyme being an excellent carrier to yield an active and stable enzymatic preparation for the acylation of the primary amine group. The amount of the acyl donor in the reaction was a key factor to achieve the mono- and chemoselective N-protection of HMFA with large excess of ethyl acetate leading to the formation of the N,O-diacetylated product.
View Article and Find Full Text PDFTetramate derivatives by chemoselective Dieckmann ring closure of -phenylserines, and their antibacterial activity.
Org Biomol Chem
May 2023
The Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, UK.
A general route which provides direct access to substituted bicyclic tetramates, making use of Dieckmann cyclisation of oxazolidine derivatives derived from -phenylserines, is reported. Of interest is the high level of diastereoselectivity observed for the -acylation reaction of oxazolidines and the complete chemoselectivity of their ring closure in the Dieckmann cyclisation. Significantly, the sense of the chemoselectivity is different to earlier reported -phenylserine systems, showing the importance of steric bulk around the bicyclic ring system.
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