478062-58-7Relevant academic research and scientific papers
An orthogonally protected α,α-bis(aminomethyl)-β-alanine building block for the construction of glycoconjugates on a solid support
Katajisto, Johanna,Karskela, Tuomas,Heinonen, Petri,Loennberg, Harri
, p. 7995 - 8001 (2007/10/03)
Synthetic glycoclusters are extensively used as mimetics of naturally occurring, multivalent carbohydrate ligands in various glycobiological applications. Their preparation, however, is far from trivial, and it still is a limiting factor in the study of carbohydrate binding. We herein report the synthesis of an orthogonally protected building block, N-Alloc-N′-Boc-N″;-Fmoc-α,α-bis (aminomethyl)-β-alanine (1), and its use in the preparation of triantennary peptide glycoclusters (21-24) on a solid support. The assembly of the clusters involves removal of the amino protections of the solid-supported branching unit 1 in the order Fmoc, Boc, and Alloc, and subsequent coupling of peracetylated O-(glycopyranosyl)-N-Fmoc-L-serine pentafluorophenyl esters (galactose, glucose, mannose, and ribose) to each amino group exposed.
