Publication

Highly branched poly(L-lysine)

2003
Journal Articles

Abstract

This paper describes the synthesis of several novel water-soluble highly branched polypeptides. The synthesis starts with the ring-opening polymerization of ε-benzyloxycarbonyl-L-lysine N-carboxyanhydride (Z-Lys NCA) or ε-trifluoroacetyl-L-lysine N-carboxyanhydride (TFA-Lys NCA), followed by end functionalization of the peptide chain with primary amine groups that can initiate the polymerization of a second generation of branches. Repetition of this ring-opening polymerization-end functionalization sequence affords highly branched poly(ε-benzyloxycarbonyl-L-lysine) (poly(Z-Lys)) and poly(ε-trifluoroacetyl-L-lysine) (poly(TFA-Lys)) in a small number of straightforward synthetic steps. Removal of the side-chain protective groups yields water-soluble and highly branched poly(L-lysine)s, which may be of potential interest for a variety of medical applications.

Official source

https://infoscience.epfl.ch/entities/publication/55b4404a-ccda-4d42-86ab-6d4c486c5e4d

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2003
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/55b4404a-ccda-4d42-86ab-6d4c486c5e4d

About this result

Related concepts (26)

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).

Polymerization

In polymer chemistry, polymerization (American English), or polymerisation (British English), is a process of reacting monomer molecules together in a chemical reaction to form polymer chains or three-dimensional networks. There are many forms of polymerization and different systems exist to categorize them. In chemical compounds, polymerization can occur via a variety of reaction mechanisms that vary in complexity due to the functional groups present in the reactants and their inherent steric effects.

Ring-opening polymerization

In polymer chemistry, ring-opening polymerization (ROP) is a form of chain-growth polymerization, in which the terminus of a polymer chain attacks cyclic monomers to form a longer polymer (see figure). The reactive center can be radical, anionic or cationic. Some cyclic monomers such as norbornene or cyclooctadiene can be polymerized to high molecular weight polymers by using metal catalysts. ROP is a versatile method for the synthesis of biopolymers. Ring-opening of cyclic monomers is often driven by the relief of bond-angle strain.

Related publications (1)

Highly branched poly(L-lysine)

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Initiation Mechanisms of an Anionic Ring Opening Polymerisation for Lactam 12