1. Solid-phase synthesis of serine-based glycosphingolipid analogues for preparation of glycoconjugate arrays
Fredrik K Wallner, Henrik A Norberg, Annika I Johansson, Mickael Mogemark, Mikael Elofsson Org Biomol Chem. 2005 Jan 21;3(2):309-15. doi: 10.1039/b415436c. Epub 2004 Dec 14.
Synthetic glycolipids with defined structures are important tools in the study of glycolipid biology. In this paper we describe a solid-phase synthesis of three galactosylated serine-based glycosphingolipid analogues using the novel linker 2-fluoro-4-(hydroxymethyl)-phenoxyacetic acid. Gel-phase (19)F-NMR spectroscopy was used to measure the yield and stereochemical outcome of the solid-phase glycosylations. Under NIS-TfOH promotion, alpha- and beta-selective glycosylations were performed at room temperature with thioglycoside donors carrying fluorine labelled protective groups. Finally, the glycolipids were covalently linked to microtiter plates and labelled lectins with different selectivity for alpha- and beta-galactosides could bind to the glycolipid arrays.
2. Improving the performance of an acid-labile 4-hydroxymethyl phenoxyacetic acid (HMP) linker on resin and SynPhase grafted solid-supports
C T Bui, F Ercole, Y Pham, R Campbell, F A Rasoul, N J Maeji, N J Ede J Pept Sci. 2000 Oct;6(10):534-8. doi: 10.1002/1099-1387(200010)6:103.0.CO;2-3.
A replacement of the acetic acid moiety by valeric acid within the 4-hydroxymethylphenoxyacetic acid (HMP) linker (Sheppard RC, Williams BJ. Acid-labile resin linkage agents for use in solid phase peptide synthesis. Int. J. Peptide Protein Res. 1982; 20: 451-454) significantly improved its performance in terms of loading capacity, yield and purity of the final products. The results indicated the spacer-linker combination and type of solid supports are important factors for solid-phase synthesis.
