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Preparation of the β 2 ‐Homoselenocysteine Derivatives Fmoc‐( S )‐ β 2 hSec(PMB)‐OH and Boc‐( S )‐ β 2 hSec(PMB)‐OH for Solution and Solid‐Phase Peptide Synthesis
Author(s) -
PatoraKomisarska Krystyna,
Jadwiga Podwysocka Dominika,
Seebach Dieter
Publication year - 2011
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201000409
Subject(s) - chemistry , peptide synthesis , peptide , amino acid , solid phase synthesis , phase (matter) , stereochemistry , protecting group , combinatorial chemistry , organic chemistry , biochemistry , alkyl
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.