Large-scale synthesis of α-amino acid-N-carboxyanhydrides

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Large-scale synthesis of α-amino acid-N-carboxyanhydrides

Heteroand homopolymers prepared from α-amino acid-N-carboxyanhydrides (NCAs) monomers are widely useful products. The preparation of pure NCA monomers has been extensively studied in the past. Purification methods including repeated crystallizations, extraction, and flash column chromatography have been devised. However, these methods are not easily amendable to large-scale NCA preparations. Th...

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Synthesis of Optically Active beta-Amino Acid N-Carboxyanhydrides.

Methodology has been developed for the general synthesis of optically active beta-amino acid N-carboxyanhydrides (beta-NCAs) through cyclization of N(beta)-Boc or N(beta)-Cbz beta-amino acids using phosphorus tribromide. The formation of beta-NCAs was confirmed by spectroscopy as well as an X-ray structural determination of beta-homoalanine-N-carboxyanhydride. The beta-NCA molecules could be po...

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Synthesis of polypeptides by ring-opening polymerization of α-amino acid N-carboxyanhydrides.

This chapter summarizes methods for the synthesis of polypeptides by ring-opening polymerization. Traditional and recently improved methods used to polymerize α-amino acid N-carboxyanhydrides (NCAs) for the synthesis of homopolypeptides are described. Use of these methods and strategies for the preparation of block copolypeptides and side-chain-functionalized polypeptides are also presented, as...

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One-pot synthesis of brush-like polymers via integrated ring-opening metathesis polymerization and polymerization of amino acid N-carboxyanhydrides.

We report here the integration of ring-opening metathesis polymerization (ROMP) and ring-opening polymerization of the amino acid N-carboxyanhydride (NCA) to allow facile synthesis of brush-like polymers containing polypeptide as the brush side chains. ROMP of N-trimethylsilyl norbornenes rendered the preparation of poly(norbornene)s bearing pendant N-TMS groups. With no need to purify the resu...

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Synthesis of thiol-clickable and block copolypeptide brushes via nickel-mediated surface initiated polymerization of α-amino acid N-carboxyanhydrides (NCAs).

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ژورنال

عنوان ژورنال: Synthetic Communications

سال: 2016

ISSN: 0039-7911,1532-2432

DOI: 10.1080/00397911.2016.1249289