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Understanding Tetrahydropyranyl as a Protecting Group in Peptide Chemistry

Published:8 March 2017 DOI: 10.1002/open.201600156 PMID: 28413747
Dr. Anamika Sharma, Dr. Iván Ramos-Tomillero, Prof. Ayman El-Faham, Prof. Ernesto Nicolas, Dr. Hortensia Rodriguez, Dr. Beatriz G. de?la?Torre, Prof. Fernando Albericio

Abstract

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 peptide chemistry. Provided here is a concise analysis of the Thp protection of various amino acid functionalities (OH, SH, NH and COOH) and its application to peptide synthesis. Thp is a useful moiety for the side-chain protection of serine, threonine and cysteine and is suitable for the Fmoc/tBu solid-phase peptide synthesis strategy. The immobilized version of 3,4-dihydro-2H-pyran, the so-called Ellman resin, is also discussed as a useful solid support for anchoring the side chains of serine, threonine and tryptophan residues.

Substances (3)

Related products
Procduct Name CAS Molecular Formula Supplier Price
3,4-Dihydro-2H-pyran 110-87-2 C5H8O 626 suppliers $10.00-$1062.00
ELLMAN'S DIHYDROPYRAN RESIN 100-200:mesh,1%DVB 28 suppliers Inquiry
Cholesterol-d7 Tetrahydropyranyl Ether C32H54O2 5 suppliers Inquiry

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