Polymer-supported biopolymer synthesis: 1. High load solid (gel) phase strategy for peptide synthesis with a phenolic poly(acryloylmorpholine)-based support

New cross-linked polyacrylic supports, functionalized with methoxywbonyl groups (from 0,2 to 6,O mmol * g-' ), were prepared. The reaction with ethylenediamine was realized in two ways: action of neat ethylenediamine or use of coupling agents. The yield depends on the initial loading with methoxycarbonyl groups and on the length of the spacer group. The percentage leading to the formation of side reactions of bridges, and that of unreactive methoxycarbonyl residues depends on steric factors. These results are of importance for the preparation of supports adapted to the solid phase peptide synthesis.

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Study of the functionalization of new acrylic polymers with ethylenediamine

Balieux

Clavelin

Daunis

et al. 1984

Makromol. Chem.

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Facile synthesis of new amine high‐loaded poly(meth)acrylamide‐based resins for solid phase peptide

Alfred

Daunis

Jacquier

1996

Macro Chemistry & Physics

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Two methods for the ready preparation of some protected primary amine-functionalized (meth)acrylamide derviatives from amino halides or amino alcohols are described. The (meth)acryloyl moiety is introduced either in the last step from unsymmetrically N,N-disubstituted diamines or, more simply, in the first step, but that demands a special work-up of the reaction mixture in order to prevent polymerization. Both methods are complementary. Reverse phase suspension polymerization of the title compounds with N-acryloylpyrrolidine and N,N-ethylenebis(acry1amide) directly affords new beaded, high-loaded aminefunctionalized resins for solid phase peptide synthesis.

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Advances in ultra‐high load polymer‐supported peptide synthesis with phenolic supports: 2. Use of ‘hydrazinolysis‐hplc’ to check for racemization on c‐terminal amino acid loading and to determine peptide homogeneity during synthesis with selectively labile c‐terminal anchoring linkages

Baker

Coffey

Epton

et al. 1988

Makromolekulare Chemie. Macromolecular Symposia

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2, 4‐Dinitrophenyl‐L‐phenylalanine has been coupled to L‐, D‐, and DL‐amino acid phenyl esters pendant upon a polymer matrix. The esters had been prepared by di‐isopropylcarbodiimide‐mediated condensation, catalyzed by 4‐dimethylaminopyridine. Reverse phase high pressure liquid chromatography (HPLC), using elution solvents consisting of 10 vol.‐% trifluoroacetic acid in water/acetonitrile mixtures, has been used to investigate the 2,4‐dinitrophenyl L‐L and L‐D dipeptide mixtures obtained on hydrazinolysis of each of the dipeptide‐matrix assemblies. ‘Hydrazinolysis‐HPLC’ has been used also to determine intermediate peptide homogeneity in ultra‐high load solid (gel) phase synthesis with Boc amino acids. Cross‐linked poly(N‐[2‐(4‐hydroxyphenyl)ethyl]acrylamide) and two derived polymers incorporating spacer groups have been used as supports. The spacer groups made possible peptide C‐terminal attachment by either HF‐labile benzyl ester or HF‐labile cyclohexyl ester bonds, while still incorporating the phenolic ester linkage susceptible to rapid hydrazinolytic scission.

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Polymer-supported biopolymer synthesis: 1. High load solid (gel) phase strategy for peptide synthesis with a phenolic poly(acryloylmorpholine)-based support

Cited by 16 publications

References 29 publications

Study of the functionalization of new acrylic polymers with ethylenediamine

Study of the functionalization of new acrylic polymers with ethylenediamine

Facile synthesis of new amine high‐loaded poly(meth)acrylamide‐based resins for solid phase peptide

Advances in ultra‐high load polymer‐supported peptide synthesis with phenolic supports: 2. Use of ‘hydrazinolysis‐hplc’ to check for racemization on c‐terminal amino acid loading and to determine peptide homogeneity during synthesis with selectively labile c‐terminal anchoring linkages

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