Trehalose-Grafted Glycopolymer: Synthesis via the Staudinger Reaction and Capture of Mycobacteria

Abstract

A new trehalose-grafted poly(2-hydroxyethyl methacrylate) (HEMA) glycopolymer was synthesized via the perfluorophenyl azide (PFPA)-mediated Staudinger reaction between poly(HEMA-co-HEMA-PFPA) and a diphenylphosphine-derivatized trehalose. The reaction occurred rapidly at room temperature without the use of any catalyst, giving the trehalose glycopolymers over 68% yield after 1 h. The grafting density of trehalose can be controlled by the copolymer composition in poly(HEMA-co-HEMA-PFPA), resulting in 6.1% (TP1) or 37% (TP2) at 10:1 and 1:1 HEMA/HEMA-PFPA feed ratio, respectively. The trehalose glycopolymer was covalently attached on glass slides or silicon wafers using a thin film of poly(HEMA-co-HEMA-PFPA) as the adhesion layer, achieved through the C−H insertion reaction of the photogenerated singlet perfluorophenyl nitrene. To demonstrate the ability of the trehalose glycopolymer to capture mycobacteria, arrays of the trehalose glycopolymer were fabricated and treated with Mycobacterium smegmatis. Results from the optical, fluorescence, and scanning electron microscopy showed that mycobacteria were indeed captured on the trehalose glycopolymer. The amount of mycobacteria captured increased with the percent trehalose in the trehalose glycopolymer and also with the concentration of the trehalose glycopolymer. In addition, the captured bacteria could be visualized by the naked eye under the illumination of a hand-held UV lamp.

Azide-Masked Fluorescence Turn-On Probe for Imaging Mycobacteria

“…Tre-Cz was prepared by coupling the amine-derivatized trehalose V (Scheme S1) − with the N -hydroxysuccinimide (NHS)-functionalized carbazole IV (Scheme S3). , The reaction was carried out at room temperature, giving Tre-Cz in 60% yield (Scheme ).…”

Click-free imaging of carbohydrate trafficking in live cells using an azido photothermal probe

“…2a ) as a trehalose analog due to its known metabolic pathway and its ability to replace natural trehalose 3 . Synthetic procedures of TreAz 24 are described in Supplementary Note 1. By FTIR spectroscopy characterization of pure TreAz powder, the azide group in TreAz shows a strong IR peak at 2,105 cm - 1 with a band width of 34 cm - 1 ( Fig.…”

“…6-GalAz (AF432) and 1-GalAz (GL631) were purchased from Synthose Inc. Gal (48260-100G-F), Ac 4 ManNAz (900917-50MG) and ManNAc (A8176-250MG) were purchased from Sigma Aldrich. TreAz was synthesized and purified according to a previous procedure 24, 53 . CaF 2 substrates (ø 25 mm and 1mm thick, CAFP25-1) were purchased from Crystran.…”