Publication

POLYETHYLENE-GLYCOL BOUND BENZYL-DERIVATIVES AND FLUORENYL-DERIVATIVES AS SOLUBILIZING SIDE-CHAIN PROTECTING GROUPS IN PEPTIDE-SYNTHESIS

1994
Journal Articles

Abstract

The covalent attachment of polyethylene glycol (PEG) to commonly used protecting groups and their use in peptide synthesis was examined. PEG bound to fluorenyl- and benzyl- type side chain protection for Lys and Glu results in increased solubility of hydrophobic peptides due to a distruption of beta-sheet conformations. PEG-protected peptides can be subject to HPLC purification and further used in convergent strategies for the synthesis of large peptides.

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1994
Journal Articles

Abstract

Official source

Related concepts (32)

Peptide synthesis

In organic chemistry, peptide synthesis is the production of peptides, compounds where multiple amino acids are linked via amide bonds, also known as peptide bonds. Peptides are chemically synthesized by the condensation reaction of the carboxyl group of one amino acid to the amino group of another. Protecting group strategies are usually necessary to prevent undesirable side reactions with the various amino acid side chains. Chemical peptide synthesis most commonly starts at the carboxyl end of the peptide (C-terminus), and proceeds toward the amino-terminus (N-terminus).

Peptide

Peptides are short chains of amino acids linked by peptide bonds. A polypeptide is a longer, continuous, unbranched peptide chain. Polypeptides which have a molecular mass of 10,000 Da or more are called proteins. Chains of fewer than twenty amino acids are called oligopeptides, and include dipeptides, tripeptides, and tetrapeptides. Peptides fall under the broad chemical classes of biological polymers and oligomers, alongside nucleic acids, oligosaccharides, polysaccharides, and others.

Protecting group

A protecting group or protective group is introduced into a molecule by chemical modification of a functional group to obtain chemoselectivity in a subsequent chemical reaction. It plays an important role in multistep organic synthesis. In many preparations of delicate organic compounds, some specific parts of their molecules cannot survive the required reagents or chemical environments. Then, these parts, or groups, must be protected. For example, lithium aluminium hydride is a highly reactive but useful reagent capable of reducing esters to alcohols.

Related publications (9)

POLYETHYLENE-GLYCOL BOUND BENZYL-DERIVATIVES AND FLUORENYL-DERIVATIVES AS SOLUBILIZING SIDE-CHAIN PROTECTING GROUPS IN PEPTIDE-SYNTHESIS

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