Synthese und anwendung von blockcopolymeren mit funktionellen gruppen in definiertem abstand unter verwendung von polyäthylenglykolen und diisocyanaten

Bayer, Ernst; Gatfield, Ian L.; Mutter, H.; Mutter, Manfred

doi:10.1016/0040-4020(78)80216-6

Cited by 14 publications

(5 citation statements)

References 10 publications

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“…PEG has proven to be the most versatile and successful polymer support for liquid-phase synthesis; however, the need still exists for further research into soluble supports. Evidence of limitations in the solubilizing power of PEG has been observed during the synthesis of longer peptides, , and a desire for increased loading capacity has been stated but in general, the water solubility of PEG limits the use of aqueous extractions as a purification technique.…”

Section: Discussionmentioning

confidence: 99%

“…Evidence of limitations in the solubilizing power of PEG has been observed during the synthesis of longer peptides, 66,67 and a desire for increased loading capacity has been stated. 94 One method has employed extraction to achieve purification of PEG-bound products; 93 but in general, the water solubility of PEG limits the use of aqueous extractions as a purification technique. Finally, PEG is insoluble in THF at low temperatures, and as the polymer is typically precipitated by addition of diethyl ether or tert-butyl methyl ether, reactions may not be conducted in these solvents.…”

Section: Discussionmentioning

confidence: 99%

Section: Copolymers Of Pegmentioning

confidence: 99%

“…To obtain a PEG-based support with increased loading capacity, block copolymers were made by linking PEG with 3,5-diisocyanatobenzyl chloride or 3-nitro-3-azapentane-1,5-diisocyanate (Figure 1). 94 The diisocyanide-containing moieties provided the additional anchoring groups for peptide synthesis through either the chloromethyl group or hydrazino group obtained by hydrogenation of the nitro group after copolymerization. Polyether blocks were made from PEG 400, 1000, 6000, or 10 000; and final copolymers ranged between 50 000 and 1 000 000 molecular weight.…”

Section: Copolymers Of Pegmentioning

confidence: 99%

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Organic Synthesis on Soluble Polymer Supports: Liquid-Phase Methodologies

1997

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Copolymers Of Pegmentioning

confidence: 99%

Section: Copolymers Of Pegmentioning

confidence: 99%

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Organic Synthesis on Soluble Polymer Supports: Liquid-Phase Methodologies

1997

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“…[13,15]) werden in 100 ml Dichlormethan (CH2CI2) gelöst und mit 20 mM J-Boc-Gly-Anhydrid [16] und 4 ml Pyridin versetzt. Die klare Lösung wird auf ca.…”

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Konformationsstudien an Partialsequenzen von ACTH und Analogen. Theoretische Vorhersagen und CD-Untersuchungen an Polyethylenglykol-gebundenen Oligopeptiden / Conformational Studies on Partial Sequences of ACTH and Analogues. Theoretical Predictions and CD Investigations of Polyethylene glycol)-bound Oligopeptides

Mutter

Bayer

1979

Zeitschrift Für Naturforschung B

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Abstract Conformational studies on synthetic segments)* of ACTH using circular dichroism (CD) are described. The segments [Val4]-ACTH (1-10) = I, [Pro1, Ala2, Ala3, Val4]-ACTH (1-10) = II and ACTH (11-23) = III have been synthesized according to the Liquid-Phase-Method with polyethylene glycol (PEG) as solubilizing C-terminal protecting group. The peptide PEG esters were studied in water and 2,2,2-trifluoroethanol (TFE) and the dependence of chain length, side chain protection and solvent upon the conformation has been evaluated. From these measurements, I shows partially helical structure in TFE and β-conformation in H2O. The modified 10-peptide II with strong helix formers at the N-terminus shows substantial amounts of helical structure in TFE and in water. A significant increase in helical structure is observed by adding the Pro residue to the N-terminus. The CD spectra of the 13-peptide III ist also typical for partially helical structure, however other types of ordered conformations cannot be excluded. The experimental data are compared with the results from calculations of the secondary structure deduced from the empirical prediction scheme of Chou and Fasman and the more elaborated statistical mechanical treatment of peptide conformations proposed by Tanaka and Scheraga. The agreement between experimental data and theoretical prediction is reason-able for I and II, whereas III is expected to adopt extended conformations beside unordered forms. The experimentally found unique behaviour of Prolin was rationalized by the asymmetric helix nucleation feature of this residue. A model for the most probable conformation of ACTH is proposed and a critical evaluation of the predictive schemes is given.

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Relationship between conformation and physicochemical properties of polypeptides. I. Synthesis of homo‐ and co‐oligopeptides by the liquid‐phase method

1980

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Glu(OBzl)]~-~,-Pro-[~-Glu(OBzl)]~ (IX). The oligomers are covalently bound to bifunctional polyethylene glycol (PEG) and monofunctional PEG-M of M , 5 X 103-2 X lo4. Analytical controls were carried out after each step of synthesis in order to ensure quantitative coupling yields. All products could he obtained in high purity as indicated by amino acid analysis, thin-layer chromatography and chiroptical methods. The solubility of the oligomers was strongly enhanced by the presence of the C-terminal PEG group, enabling conformational investigations in a variety of solvents. A significant relationship between conformation and physicochemical properties of the oligopeptides was observed. Oligomers with tendencies to adopt a-helical (1,II) or unordered structures (VI-IX) showed no pronounced change in solubility or coupling kinetics during chain elongation, whereas the onset of a P-structure (IV,V) was paralleled by a drastic decrease in solubility and reactivity of the terminal amino groups. Most notably, the insertion of a proline or glycine in the middle of a P-forming peptide chain (V1,VII) resulted in a considerable increase in solubility compared to the corresponding homo-oligomers. The impact of the conformational properties of a peptide chain on strategic considerations of peptide synthesis in solution is delineated.

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Synthese und anwendung von blockcopolymeren mit funktionellen gruppen in definiertem abstand unter verwendung von polyäthylenglykolen und diisocyanaten

Cited by 14 publications

References 10 publications

Organic Synthesis on Soluble Polymer Supports: Liquid-Phase Methodologies

Organic Synthesis on Soluble Polymer Supports: Liquid-Phase Methodologies

Relationship between conformation and physicochemical properties of polypeptides. I. Synthesis of homo‐ and co‐oligopeptides by the liquid‐phase method

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