317366-29-3Relevant academic research and scientific papers
Synthesis of achiral α,α-bis(aminomethyl)-β-alanines and their use in the preparation of branched β-peptide conjugates of N-2-alkyl-1,2,3,4-tetrahydroisoquinolines on solid support
Heinonen, Petri,Rosenberg, Jaana,Loennberg, Harri
, p. 3647 - 3652 (2000)
Three achiral branching units 1-3 derived from α,α-bis(aminomethyl)-β-alanine were synthesized and evaluated in the construction of branched and sterically compact β-peptide conjugates on a solid support. Several peptide conjugates bearing an N-alkylated 1,2,3,4-tetrahydroisoquinoline moiety were prepared to demonstrate the applicability of the branching units in a solid phase peptide synthesis. The most useful building block 3 incorporated Boc-protected aminomethyl side chains at the α-carbon of N-phthaloyl-β-alanine.
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.
