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Preparation of the β2-Homoselenocysteine Derivatives Fmoc-(S)-β2hSec(PMB)-OH and Boc-(S)-β2hSec(PMB)-OH for Solution and Solid-Phase Peptide Synthesis

✍ Scribed by Krystyna Patora-Komisarska; Dominika Jadwiga Podwysocka; Dieter Seebach

Publisher
John Wiley and Sons
Year
2011
Tongue
German
Weight
318 KB
Volume
94
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Fmoc‐β^2^hSer(^t^Bu)‐OH was converted to Fmoc‐β^2^hSec(PMB)‐OH in five steps. To avoid elimination of HSeR, the selenyl group was introduced in the second last step (Fmoc__‐β__^2^hSer(Ts)‐OAll→Fmoc‐β^2^hSec(PMB)‐OAll). In a similar way, the N‐Boc‐protected compound was prepared. With the β^2^hSe‐derivatives, 21 β^2^‐amino‐acid building blocks with proteinogenic side chains are now available for peptide synthesis.

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