Ueber die Glycin‐carbonsäure

Leuchs, Hermann

doi:10.1002/cber.190603901133

Cited by 312 publications

(138 citation statements)

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“…The ROP of NCAs has already been used for the synthesis of polypeptides with various applications that range from drug delivery systems [68], tissue engineering [69], sensing [70] to catalysis [71]. The first NCA [72][73][74] were synthesised by Leuchs in 1906. Since then, a plethora of polypeptides has been created due to the variety of natural and non-natural amino acids and the versatility of the polymerisation method, as it has been reviewed in the following excellent literature [48][49][50].…”

Section: Ring-opening Polymerisation (Rop) Of α-Amino Acid N-carboxyamentioning

confidence: 99%

Peptide-Based Polymer Therapeutics

2014

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Abstract:Polypeptides are envisaged to achieve a major impact on a number of different relevant areas such as biomedicine and biotechnology. Acquired knowledge and the increasing interest on amino acids, peptides and proteins is establishing a large panel of these biopolymers whose physical, chemical and biological properties are ruled by their controlled sequences and composition. Polymer therapeutics has helped to establish these polypeptide-based constructs as polymeric nanomedicines for different applications, such as disease treatment and diagnostics. Herein, we provide an overview of the advantages of these systems and the main methodologies for their synthesis, highlighting the different polypeptide architectures and the current research towards clinical applications.

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Section: Ring-opening Polymerisation (Rop) Of α-Amino Acid N-carboxyamentioning

confidence: 99%

Peptide-Based Polymer Therapeutics

2014

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“…5 The polymerization was initiated with triethylamine and was completed in about one day at room temperature. The molecular weights of PBLG and PBDG, which were computed from the relation of intrinsic viscosity and molecular weight, were 170,000 and 150,000, respectively.…”

Section: Synthesis and Specimenmentioning

confidence: 99%

Transition of Mixture of Poly(γ-benzyl L-glutamate) and Poly(γ-benzyl D-glutamate)

Yoshikawa

Tsujita

Uematsu

et al. 1975

Polym J

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ABSTRACT:Mixture of poly(r-benzyl L-glutamate) and poly(r-benzyl o-glutamate) have a special interaction between the benzyl groups at the end of the side chain and have different properties from the pure enantiomorphic form of poly(r-benzyl glutamate). A reversible first-order transition has been observed and ascribed to the formation and breakdown of stackings of the benzyl groups at the end of the side chain. The isothermal transition was investigated by dilatometry and studied in light of present concepts of crystallization in crystalline polymers. Plots of extent of isothermal transition vs. time were sigmoidal in shape and fitted the Avrami equation. The exponent in the A vrami equation was 4. The reciprocal half-time of the transition was taken as a measure of the overall rate of transition. Plots of logarithm of transition rate against Tm[T(Tm-T)]-1 and Tm2[T(Tm-T)2]-I, whereTm is the temperature for the breakdown of stacking of the benzyl groups, taken as 100.2°C, and Tis the stack formation temperature, gave reasonably good straight lines. Thus, as is usually found with polymers, no discrimination could be made between two possible mechanisms of the transition; two-dimensional or three-dimensional nucleations.KEY WORDS The structure of the racemic form of poly(rbenzyl glutamate) (PBG) is different from that of pure poly(r-benzyl L-glutamate) (PBLG) or pure poly(r-benzyl n-glutamate) (PBDG). 1 ' 2 ' 3 The structural studies on the racemic form of PBG have revealed that regular side-chain conformations are formed between the benzyl groups; stackings of the benzyl groups at the end of the side chain are formed between neighbouring PBLG and PBDG molecules.in light of present concepts of crystallization in crystalline polymers. EXPERIMENTAL Synthesis and Specimenr-benzyl glutamate N-carboxyanhydride (NCA) was prepared by the method proposed by Leuch. 5 The polymerization was initiated with triethylamine and was completed in about one day at room temperature. The molecular weights of PBLG and PBDG, which were computed from the relation of intrinsic viscosity and molecular weight, were 170,000 and 150,000, respectively. Some studies of the transition due to the breakdown of stacking in the racemic mixture of PBG have been reported by Fukuzawa, et al. 4 From thermal analysis and dilatometric measurements, a first-order transition was observed at about 95°C. In this paper the kinetics of the formation of stacking is investigated and studied * To whom correspondence should be addressed. 96The mixtures of PBLG and PBDG were dissolved in 1,2-dichloroethane at a concentration below 0.05 (wjv). Films 0.01-cm thick were cast at room temperature from the solution. Specimens were heated once to 140°C and then cooled

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“…Numerous reports on the methodology for the synthesis of polypeptides have been published [1][2][3][4][5][6][7][8][9][10][11][12][13][14]. The N-carboxyl--amino acid anhydride (NCA) method (1) [2,3,9,10], polymerization of amino acids using active esters (2) [1,[4][5][6][7], solid-phase peptide synthesis (3) [8,12], and the heating of amino acids (4) [13,14] are typical examples. The NCA method (1) is suitable for making homopolypeptides and random copolypeptides but is not suitable for the synthesis of sequential copolyamino acid, which is more important for the build-up of functional polypeptides.…”

Section: Introductionmentioning

confidence: 99%

Thermal Synthesis of Polypeptides from N-Butyloxycarbonyl Oligopeptides Containing Aspartyl Residue at C-Terminus

Munegumi

Yamada

2017

International Journal of Polymer Science

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The thermal reactions of amino acids have been investigated for pure organic synthesis, materials preparation in industry, and prebiotic chemistry. N-t-Butyloxycarbonyl aspartic acid (Boc-Asp) releases 2-butene and carbon dioxide upon heating without solvents. The resulting mixture of the free molten aspartic acid was dehydrated to give peptide bonds. This study describes the thermal reactions of N-t-butyloxycarbonyl peptides (Boc-Gly-L-Asp, Boc-L-Ala-L-Asp, Boc-L-Val-L-Asp, and Boc-Gly-Gly-L-Asp) having an aspartic residue at the carboxyl terminus. The peptides were deprotected upon heating at a constant temperature between 110 and 170°C for 1 to 24 h to afford polypeptides in which the average molecular weight reached 7800.

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Ueber die Glycin‐carbonsäure

Cited by 312 publications

References 4 publications

Peptide-Based Polymer Therapeutics

Peptide-Based Polymer Therapeutics

Transition of Mixture of Poly(γ-benzyl L-glutamate) and Poly(γ-benzyl D-glutamate)

Thermal Synthesis of Polypeptides from N-Butyloxycarbonyl Oligopeptides Containing Aspartyl Residue at C-Terminus

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