Sharma Anamika, Ramos-Tomillero Iván, El-Faham Ayman, Rodríguez Hortensia, de la Torre Beatriz G, Albericio Fernando
Catalysis and Peptide Research Unit School of Health Sciences University of KwaZulu-Natal Durban 4001 South Africa.
Inorganic and Organic Department University of Barcelona Martí Franqués 1-11 08028 Barcelona Spain.
ChemistryOpen. 2017 Mar 8;6(2):206-210. doi: 10.1002/open.201600157. eCollection 2017 Apr.
The use of the tetrahydropyranyl (Thp) group for the protection of serine and threonine side-chain hydroxyl groups in solid-phase peptide synthesis has not been widely investigated. Ser/Thr side-chain hydroxyl protection with this acid-labile and non-aromatic moiety is presented here. Although Thp reacts with free carboxylic acids, it can be concluded that to introduce Thp ethers at the hydroxyl groups of N-protected Ser and Thr, protection of the C-terminal carboxyl group is unnecessary due to the lability of Thp esters. Thp-protected Ser/Thr-containing tripeptides are synthesized and the removal of Thp studied in low concentrations of trifluoroacetic acid in the presence of cation scavengers. Given its general stability to most non-acidic reagents, improved solubility of its conjugates and ease with which it can be removed, Thp emerges as an effective protecting group for the hydroxyl groups of Ser and Thr in solid-phase peptide synthesis.
在固相肽合成中，使用四氢吡喃基（Thp）保护丝氨酸和苏氨酸侧链羟基的研究尚未广泛开展。本文介绍了用这种对酸不稳定且无芳香性的基团对Ser/Thr侧链羟基进行保护。尽管Thp会与游离羧酸反应，但可以得出结论，由于Thp酯的不稳定性，在N-保护的Ser和Thr的羟基上引入Thp醚时，无需保护C端羧基。合成了含Thp保护的Ser/Thr的三肽，并在阳离子清除剂存在的情况下，研究了在低浓度三氟乙酸中Thp的去除情况。鉴于其对大多数非酸性试剂具有普遍稳定性、其共轭物的溶解性有所改善以及易于去除，Thp成为固相肽合成中Ser和Thr羟基的有效保护基团。
