Polymerization reaction with diphenylphosphoryl azide. Preparation of sequential polypeptides by direct polycondensation of peptides

Nishi, Norio; Naruse, Takumi; Hagiwara, Keisuke; Nakajima, Bun-ichiro; Tokura, Seiichi

doi:10.1002/macp.1991.021920814

Cited by 30 publications

(18 citation statements)

References 22 publications

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“…DPPA (5.64 mmol) and triethylamine (TEA; 9.4 mmol) were added to a stirred solution of TFA − H

_{+}^{2}

K(Z)GGVG–OH (3.76 mmol) in DMSO (3.76 mL) 11. The resulting mixture was kept at room temperature for 4 days, and then the polymer was precipitated by the addition of diethyl ether.…”

Section: Methodsmentioning

confidence: 99%

Chemical synthesis of cross-linked poly(KGGVG), an elastin-like biopolymer

Martino

Tamburro

2001

Biopolymers

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Previous studies afforded on peptides and polypeptides containing repetitive sequences of elastin have largely demonstrated that their molecular and supramolecular properties are fully representative of those of tropoelastin, the soluble, linear precursor of elastin itself. In the attempt to synthesize cross‐linked elastin‐mimetic polypeptides, the repeating sequence VGGVG (V: valine; G: glycine), typical of elastin, was modified to incorporate lysine residues, yielding the polymer poly(KGGVG) (K: lysine). This imparts primary amine functionality susceptible to cross‐linking reaction with appropriate bifunctional cross‐linking reagents. We report herein the chemical synthesis and cross‐linking of poly(KGGVG) with glutaraldehyde (GTA) and with disuccinimidyl glutarate (DSG). In both cases, the characterization of the polymers, both linear and cross‐linked, has been carried out by CD spectroscopy and transmission electron microscopy measurements. The obtained results, although not conclusive, demonstrate that poly(KGGVG), both linear and cross‐linked, may be considered very similar to tropoelastin and mature elastin, as concerns its molecular and supramolecular properties. © 2001 John Wiley & Sons, Inc. Biopolymers 59: 29–37, 2001

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“…DPPA (5.64 mmol) and triethylamine (TEA; 9.4 mmol) were added to a stirred solution of TFA − H

_{+}^{2}

K(Z)GGVG–OH (3.76 mmol) in DMSO (3.76 mL) 11. The resulting mixture was kept at room temperature for 4 days, and then the polymer was precipitated by the addition of diethyl ether.…”

Section: Methodsmentioning

confidence: 99%

Chemical synthesis of cross-linked poly(KGGVG), an elastin-like biopolymer

Martino

Tamburro

2001

Biopolymers

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“…26 The N-protected peptide, Boc-Leu-L'.lzPhe-Pro-OH (Boe, t-butoxycarbonyl), was prepared by ring-opening Boc-L'.lzPhe azlactone with amino group of Pro. The tripeptide was checked for purity by 1 H NMR and TR spectroscopy, thin-layer chromatography (TLC), and gel permeation chromatography (GPC).…”

Section: Methodsmentioning

confidence: 99%

Design of Novel Helical Backbone. Conformational Energy Calculation and Synthesis of Sequential Polypeptide Containing Z-Dehydrophenylalanine and Proline Residues

Inai

Sakakura

Hirabayashi

1997

Polym J

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ABSTRACT:Theoretical conformational analysis was carried out on periodic polypeptides containing Z-dehydrophenylalanine (LJzPhe) and Pro residues, poly(X-LJzPhe-Pro) (X=Ala, Leu, Gly, o-Ala, and aminoisobutyric acid (Aib)), using the procedure of conformational energy minimization. The lowest-energy conformations were found to be a right-handed ,B 11 · 9 -helix for X=Ala, and a right-handed /15·'-helix for X=Gly. For X=Leu, D-Ala, and Aib, the lowest-energy conformation was found to be a left-handed ,8 6 1 -6 · 2 -helix: the nearest phenyl-phenyl pairs took a center-to-center distance of 6.6~6.8 A and an edge-to-edge orientation. On the whole, phenyl groups were arranged in C 2 -type symmetry on the helical wheel. Poly(Leu-LJzPhe-Pro) was synthesized by polymerizing the corresponding tripeptide with diphenylphosphoryl azidc. The polypeptide in chloroform and in tetrahydrofuran showed a positive CD signal around 280 nm, which is ascribed to the absorption band of L1 2 Phe residue. This CD pattern means that the screw angle between neighboring ,1 2 Phe transition moments is around 0° or 180°, suggesting the ,8 6 -helical conformation predicted above.KEY WORDS Sequential Polypeptide / Z-Dehydrophenylalanine / Praline / Conformational Energy Calculation / Synthesis / CD Study / ,B-Helix /

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“…Moreover, some impurities containing unfunctionalized or monofunctionalized species are generated in these reactions, which their presence in the polymerization flask causes a significant decrease in molecular weight of the final products. The details about various aspects of this one-pot polyaddition were reported in literature [25]. As listed in Table 1, the resulting dark yellow to brown poly(imide-urea)s possessed inherent viscosities ranging between 0.10 dL/g and 0.22 dL/g, measured in DMAc at a concentration of 0.5 g/dL at 30˚C.…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

Organosoluble and Thermally Stable of Benzazole-Containing Poly(Imide-Urea)s: One-Pot Synthesis and Characterization

Toiserkani¹

2011

OJPChem

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The preparation of new types of poly(imide-urea)s (PIUs) with high thermal stability and improved solubility was investigated. Three series of aromatic poly(imide-urea)s (PIU O a-c, PIU S a-c, and PIU N a-c) bearing pendent benzoxazole, benzothiazole or benzimidazole rings were prepared by one-pot polycondensation reaction of three bis(imide-carboxylic acid)s, 2-[3,5-bis(N-trimellitimidoyl)-phenyl]benzoxazole (1 O), 2-[3,5-bis(Ntrimellitimidoyl)-phenyl]benzothiazole (1 S), or 2-[3,5-bis(N-trimellitimidoyl)-phenyl]benzimidazole (1 N) with various kinds of aromatic diamines (a-c). The effects of the benzazole pendent groups on the polymer properties such as solubility and thermal stability were investigated by comparison of the polymers. All of the resulting polymers exhibited excellent solubility in common polar solvents. The glass transition temperature of the polymers determined by DSC thermograms were in the range 192˚C-236˚C. The temperatures at 10% weight loss from their TGA curves were found to be in the range 390˚C-441˚C in nitrogen.

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Polymerization reaction with diphenylphosphoryl azide. Preparation of sequential polypeptides by direct polycondensation of peptides

Cited by 30 publications

References 22 publications

Chemical synthesis of cross-linked poly(KGGVG), an elastin-like biopolymer

Chemical synthesis of cross-linked poly(KGGVG), an elastin-like biopolymer

Design of Novel Helical Backbone. Conformational Energy Calculation and Synthesis of Sequential Polypeptide Containing Z-Dehydrophenylalanine and Proline Residues

Organosoluble and Thermally Stable of Benzazole-Containing Poly(Imide-Urea)s: One-Pot Synthesis and Characterization

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