Synthesis of pyrrolidine-2,4-diones from urethane N-carboxyanhydrides (UNCAs)

Pothion, Catherine; Fehrentz, Jean‐Alain; Aumelas, André; Loffet, A.; Martinez, Jean

doi:10.1016/0040-4039(95)02367-4

Cited by 19 publications

(14 citation statements)

References 7 publications

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“…In the presence of a base in aprotic medium, UNCAs led to N-urethane protected-3,5-dialkyl-3-amino pyrrolidine-2,4-diones 63 (Pothion et al, 1996;Leban and Colson, 1996). Consequently the choice of the base should be carefully considered to optimize yields and avoid side products when UNCAs are used in peptide synthesis or in reactions with slow reactivity nucleophiles.…”

Section: Synthesis Of Amino Arid Derivatives From N-protected Carboxymentioning

confidence: 98%

Some of the amino acid chemistry going on in the Laboratory of Amino Acids, Peptides and Proteins

et al. 1999

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Some of the chemistry of amino acids going on in our laboratory (Laboratoire des Amino acides Peptides et Protéines) is described as well as some mass spectrometry methodology for their characterization particularly on solid supports. Several aspects are presented including: (i) the stereoselective synthesis of natural and unnatural amino acids using 2-hydroxypinan-3-one as chiral auxiliary; (ii) the stereoselective synthesis of natural and unnatural amino acids by deracemization of alpha-amino acids via their ketene derivatives; (iii) the synthesis of alpha-aryl-alpha-amino acids via reaction of organometallics with a glycine cation; (iv) the diastereoselective synthesis of glycosyl-alpha-amino acids; (v) the synthesis of beta-amino acids using alpha-aminopyrrolidinopiperazinediones as chiral templates; (vi) the reactivity of urethane-N-protected N-carboxyanhydrides. To characterize natural and non natural amino acids through their immonium ions by mass spectrometry, some methodology is also described.

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Section: Synthesis Of Amino Arid Derivatives From N-protected Carboxymentioning

confidence: 98%

Some of the amino acid chemistry going on in the Laboratory of Amino Acids, Peptides and Proteins

et al. 1999

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“…[63,64] Compound 9 is such a dimerization product derived from Boc-Phe-NCA. Finally, it should be mentioned that N-protected b-amino acid NCAs such as 10 and 11 were also synthesized.…”

Section: Stepwise Peptide Synthesesmentioning

confidence: 99%

Polypeptides and 100 Years of Chemistry of α‐Amino Acid N‐Carboxyanhydrides

2006

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Syntheses and polymerizations of alpha-amino acid N-carboxyanhydrides (NCAs) were reported for the first time by Hermann Leuchs in 1906. Since that time, these cyclic and highly reactive amino acid derivatives were used for stepwise peptide syntheses but mainly for the formation of polypeptides by ring-opening polymerizations. This review summarizes the literature after 1985 and reports on new aspects of the polymerization processes, such as the formation of cyclic polypeptides or novel organometal catalysts. Polypeptides with various architectures, such as diblock, triblock, and multiblock sequences, and star-shaped or dendritic structures are also mentioned. Furthermore, lyotropic and thermotropic liquid-crystalline polypeptides will be discussed and the role of polypeptides as drugs or drug carriers are reviewed. Finally, the hypothetical role of NCAs in molecular evolution on the prebiotic Earth is discussed.

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“…[63,64] Formel 9 repräsentiert ein solches Dimerisierungsprodukt, das aus Boc-Phe-NCA hergestellt wurde. Abschließend soll erwähnt werden, dass auch N-geschützte bAminosäure-NCAs (z.…”

Section: Introductionunclassified

Polypeptide und 100 Jahre Chemie der α‐Aminosäure‐N‐carboxyanhydride

Kricheldorf

2006

Angewandte Chemie

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Synthese und Polymerisation von α‐Aminosäure‐N‐carboxyanhydriden (NCAs) wurden erstmals im Jahre 1906 von Herrmann Leuchs beschrieben. Seit dieser Zeit wurden diese cyclischen, sehr reaktiven α‐Aminosäurederivate mehrfach zur schrittweisen Peptidsynthese eingesetzt, sie wurden aber vor allem zur Herstellung von Polypeptiden durch ringöffnende Polymerisation (ROP) verwendet. Es werden nun neue Aspekte der ringöffnenden Polymerisation diskutiert, z. B. die Verwendung neuartiger metallorganischer Initiatoren oder die Entstehung cyclischer Polypeptide. Des Weiteren werden Architekturen wie Diblock‐, Triblock‐ und Multiblockcopolymere sowie sternförmige oder hochverzweigte Polypeptide vorgestellt. Ferner werden lyotrope und thermotrope Polypeptide sowie die Verwendung von Polypeptiden als Pharmaka oder Pharmakaträger besprochen. Schließlich wird die Rolle von NCAs im Konzept der molekularen Evolution diskutiert.

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Synthesis of pyrrolidine-2,4-diones from urethane N-carboxyanhydrides (UNCAs)

Cited by 19 publications

References 7 publications

Some of the amino acid chemistry going on in the Laboratory of Amino Acids, Peptides and Proteins

Some of the amino acid chemistry going on in the Laboratory of Amino Acids, Peptides and Proteins

Polypeptides and 100 Years of Chemistry of α‐Amino Acid N‐Carboxyanhydrides

Polypeptide und 100 Jahre Chemie der α‐Aminosäure‐N‐carboxyanhydride

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