A1 Vertaisarvioitu alkuperäisartikkeli tieteellisessä lehdessä
An orthogonally protected alpha,alpha-bis(aminomethyl)-beta-alanine building block for the construction of glycoconjugates on a solid support
Tekijät: Katajisto J, Karskela T, Heinonen P, Lonnberg H
Kustantaja: AMER CHEMICAL SOC
Julkaisuvuosi: 2002
Lehti:: Journal of Organic Chemistry
Tietokannassa oleva lehden nimi: JOURNAL OF ORGANIC CHEMISTRY
Lehden akronyymi: J ORG CHEM
Vuosikerta: 67
Numero: 23
Aloitussivu: 7995
Lopetussivu: 8001
Sivujen määrä: 7
ISSN: 0022-3263
DOI: https://doi.org/10.1021/jo026053b
Tiivistelmä
Synthetic glycoclusters are extensively used as mimeties 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-alpha,alpha-bis(amino- methyl)-beta-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.
Synthetic glycoclusters are extensively used as mimeties 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-alpha,alpha-bis(amino- methyl)-beta-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.
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