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Solid-Phase Synthesis of a Sialyl-Tn-Glycoundecapeptide of the MUC1 Repeating Unit

✍ Scribed by Beate Liebe; Horst Kunz

Book ID
102861467
Publisher
John Wiley and Sons
Year
1997
Tongue
German
Weight
751 KB
Volume
80
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The synthesis of glycopeptides carrying tumour‐associated antigens is of interest for cancer diagnosis and treatment. Here, a very efficient route lo disaccharide threonine building block 8 is presented which allows the introduction of the sialyl‐Tn antigen into a peptide. The syntheses of the undecapeptide and the sialyl‐Tn‐containing glycoundecapeptide, which are a part of the repeating unit of MUC1, were performed by solid‐phase synthesis with an allylic anchor cleavable under neutral conditions. After detachment from the resin, the peptide and the glycopeptide arc completely deprotected giving the target compounds 13 and 15, respectively.

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✍ Dipl.-Chem. Beate Liebe; Prof. Dr. Horst Kunz πŸ“‚ Article πŸ“… 1997 πŸ› John Wiley and Sons 🌐 English βš– 489 KB πŸ‘ 2 views

Although no evidence of a-haloalkylsamarium formation has been obtained, a reactive cc-iodoethyl species is undoubtedly generated in an optically active form. In conclusion, the reaction of 1,l-diiodoalkanes with samarium(l1) diiodide in the presence of chiral aldehydes produces a-haloaikyl building