Tetrahydropyranyl: A Non‐aromatic, Mild‐Acid‐Labile Group for Hydroxyl Protection in Solid‐Phase Peptide Synthesis
نویسندگان
چکیده
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.
منابع مشابه
Understanding Tetrahydropyranyl as a Protecting Group in Peptide Chemistry
Tetrahydropyranyl (Thp) is recognized as a useful protecting group for alcohols in organic synthesis. It has several advantages, including low cost, ease of introduction, general stability to most non-acidic reagents, it confers good solubility, and the ease with which it can be removed if the functional group it protects requires manipulation. However, little attention has been paid to Thp in ...
متن کاملAmmonium Decatungstocerate(IV): An Efficient Catalyst for the Protection and Deprotection of Tetrahydropyranyl Ethers
In multi-step organic syntheses, the protection and deprotection of tetrahydropyranyl (THP) ethers is one of the most frequently used methods. Over the years, different methods have been used from various catalytic systems for the protection of hydroxyl groups as THP ethers and their deprotection. Herein we have reported that various alcohols and phenols have been efficiently converted to the c...
متن کاملPii: S0040-4039(99)01563-4
The 9-phenylthioxanthyl (S-pixyl or S-Px) group has been investigated as a photocleavable protecting group for primary alcohols, and specifically as a 5' hydroxy protecting group for deoxyribonucleosides. Several alcohols, including the four nucleosides with protected exocyclic amino functions, were protected in very good to excellent yield by treatment of 9-chloro-9-phenylthioxanthene 3 in dry...
متن کاملGraphene–ZnO@SiO2 hybrid: An efficient and solid acid catalyst for synthesis of azlactones under ultrasound irradiation
The central theme of this article is how to explore a novel route to fabricate graphene– ZnO@SiO2 hybrid by a covalent process. The synthesis procedure consists of three-steps: (1) synthesis of ZnO nanoparticles, (2) ZnO nanoparticles modification by tetraethyl orthosilicate and (3-aminopropyl) triethoxysilane after introduction of amino groups on its surface, (3) the covalent attach...
متن کاملGraphene–ZnO@SiO2 hybrid: An efficient and solid acid catalyst for synthesis of azlactones under ultrasound irradiation
The central theme of this article is how to explore a novel route to fabricate graphene– ZnO@SiO2 hybrid by a covalent process. The synthesis procedure consists of three-steps: (1) synthesis of ZnO nanoparticles, (2) ZnO nanoparticles modification by tetraethyl orthosilicate and (3-aminopropyl) triethoxysilane after introduction of amino groups on its surface, (3) the covalent attach...
متن کامل