628. Synthetic polypeptides. Part II. Properties of oxazolid-2 : 5-diones and an initial study of the preparation of polypeptides there-from

Coleman, Daniel; Farthing, A. C.

doi:10.1039/jr9500003218

Cited by 29 publications

(15 citation statements)

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“…NCA polymerization into peptides has already been described in the literature, whether in the solid phase or in aqueous solutions (Coleman and Farthing 1950;Curtius et al 1930;Farthing and Reynolds 1950). However, these studies have been conducted in a synthetic scope, starting from carefully purified materials.…”

Section: Prebiotic Implicationsmentioning

confidence: 99%

N-Carbamoyl Amino Acid Solid–Gas Nitrosation by NO/NO x : A New Route to Oligopeptides via α-Amino Acid N-Carboxyanhydride. Prebiotic Implications

et al. 1999

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Alpha-N-Carbamoyl amino acid (CAA), whose conditions of formation in a prebiotic hydrosphere have been described previously (Taillades et al. 1998), could have been an important intermediate in prebiotic peptide synthesis through reaction with atmospheric NOx. Nitrosation of solid CAA (glycine or valine derivative) by a 4/1 NO/O2 gaseous mixture (1 atm) yields N-carboxyanhydride (NCA) quantitatively in less than 1 h at room temperature. The crude solid NCA undergoes quantitative oligomerization (from trimer to nonamer under the conditions we used) when treated with a (bi)carbonate aqueous buffer at pH 9. We therefore suggest that part of the prebiotic amino acid activation/polymerization process may have taken place in a dry phase ("drying-lagoon" scenario).

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Section: Prebiotic Implicationsmentioning

confidence: 99%

N-Carbamoyl Amino Acid Solid–Gas Nitrosation by NO/NO x : A New Route to Oligopeptides via α-Amino Acid N-Carboxyanhydride. Prebiotic Implications

et al. 1999

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“…The molecular weight of the resulting Co-polymer was determined by osmometry in benzene solution, and in this solvent an extensive agglomeration of the investigated polyaminoacids takes place. The analysis of the end groups by COLEMAN and FARTHING (29) and by other investigators (30) proved that the degree ofpolymerisation of such a polypeptide does not exceed 100.…”

Section: Initiation Of "Normal" Nca's Polymerisation By Other Agentsmentioning

confidence: 99%

The kinetics and mechanism of N-carboxy-α-amino-acid anhydride (NCA) polymerisation to poly-amino acids

Szwarc¹

1965

Advances in Polymer Science

124

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“…The usual routes to NCA are the well‐known Curtius4 and Fuchs–Farthing reactions. (Scheme )5, 6 Both present the disadvantage of handling hazardous species such as phosgene and the difficulty of separating by‐products that are harmful to the polymerisation processes. Despite many efforts to improve both routes7 these drawbacks have remained unsolved.…”

Section: Introductionmentioning

confidence: 99%

From prebiotic macromolecules to synthetic polypeptides: a new, efficient synthesis of α‐amino acid N‐carboxyanhydrides (NCAs)

Boiteau

Collet

Lagrille

et al. 2002

Polymer International

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While polypeptide materials present important application potentialities, the expense of amino acid N‐carboxyanhydride (NCA) monomers strongly limits their applications. We present here a new, promising synthetic route to NCA through N‐carbamoylamino acid nitrosation by gaseous NOx(1 < x < 2) in the solid–gas phase. This very efficient reaction (which was originally developed in a prebiotic context) works in the absence of solvent and with minimum waste, and presents interesting economic features. Some mechanistic investigations aimed at the optimisation and scale‐up of this reaction in the solid‐gas phase are presented. © 2002 Society of Chemical Industry

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628. Synthetic polypeptides. Part II. Properties of oxazolid-2 : 5-diones and an initial study of the preparation of polypeptides there-from

Cited by 29 publications

References 0 publications

N-Carbamoyl Amino Acid Solid–Gas Nitrosation by NO/NO x : A New Route to Oligopeptides via α-Amino Acid N-Carboxyanhydride. Prebiotic Implications

N-Carbamoyl Amino Acid Solid–Gas Nitrosation by NO/NO x : A New Route to Oligopeptides via α-Amino Acid N-Carboxyanhydride. Prebiotic Implications

The kinetics and mechanism of N-carboxy-α-amino-acid anhydride (NCA) polymerisation to poly-amino acids

From prebiotic macromolecules to synthetic polypeptides: a new, efficient synthesis of α‐amino acid N‐carboxyanhydrides (NCAs)

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