1. N-Thiohydroxy Succinimide Esters (NTSEs): Versatile Reagents for Selective Acyl and Acylthio Transfer
Yun-Feng Li, Ya-Feng Wei, Jun Tian, Juan Zhang, Hong-Hong Chang, Wen-Chao Gao Org Lett. 2022 Aug 12;24(31):5736-5740. doi: 10.1021/acs.orglett.2c02160. Epub 2022 Jul 29.
Differentiation between similarly reactive sites in molecules represents an ongoing challenge of organic synthesis. Herein we described one kind of versatile reagents, N-thiohydroxy succinimide esters (NTSEs), serving as both acyl and acylthio surrogates for the diverse synthesis of ketones, thioesters, amides, and acyl disulfides by selective cleavage of similarly reactive C-S and N-S bonds.
2. N-(2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-alpha-D-galactopyranosyloxy)succinimide
O Renaudet, P Dumy, C Philouze, M T Averbuch-Pouchot Acta Crystallogr C. 2001 May;57(Pt 5):649-50. doi: 10.1107/s0108270101003377. Epub 2001 May 15.
The crystal structure of the title compound, C18H24N2O11, a GalNAc mimic containing an alpha-glycosyloxysuccinimide linkage, has been determined. The pyranose ring geometry is an almost perfect (4)C(1) chair. The torsion angle of the exocyclic hydroxymethyl group is shown to be gauche-trans with respect to O1 and C4, respectively.
3. Labeling a protein with fluorophores using NHS ester derivitization
Jagpreet S Nanda, Jon R Lorsch Methods Enzymol. 2014;536:87-94. doi: 10.1016/B978-0-12-420070-8.00008-8.
N-hydroxysuccinimde (NHS) ester-mediated derivitization involves the reaction of this amine-reactive group with the primary amines of a protein or a biomolecule. Using NHS chemistry allows one to conjugate various fluorescent probes, biotin, and cross-linkers to primary amines. For example, we use NHS ester chemistry to fluorescently label the amino terminus of a protein with the dye, 5-(and-6)-carboxyfluorescein, succinimidyl ester (5(6)-FAM, SE).
