The Formation of Polypeptides by Rearrangement of α-Carboxy Hydroxamic Acids

Hurd, Charles D.; Buess, Charles M.

doi:10.1021/ja01150a001

Cited by 23 publications

(13 citation statements)

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“…To date, some useful monomers for polypeptides synthesis have been reported. For example, Hurd and Buess developed a-carboxy hydroxamic acid for synthesis of polypeptides, 15 and Ehler and Orgel used N-imidazolylcarboxyl amino acid as precursor of NCA. 16 Also, we previously reported selective synthesis of NCA and polypeptides through N-(4-nitrophenyloxycarbonyl) amino acid.…”

Section: Introductionmentioning

confidence: 99%

Useful synthetic method of polypeptides with well‐defined structure by polymerization of activated urethane derivatives of α‐amino acids

Yamada¹,

Koga²,

Endō³

2012

J. Polym. Sci. A Polym. Chem.

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Cancer in adolescents and young adults is an important public health issue, because there are approximately 1 million new cases annually. The distribution of diseases in this age group varies geographically, contributing to differences in survival rates. Although an overall survival rate exceeding 80 % has been reported in optimal circumstances, emerging knowledge about distinctions in tumor biology and enhanced clinical accrual to clinical trials should lead to further gains. The challenges of cancer survivorship demand further attention with a particular focus on the quality of life of survivors and amelioration of the long‐term complications of treatment. Programs in cancer screening and prevention provide potential for considerable benefits in this age group. A renewed perspective on the adolescent and young adult cohort is required; and, in all of these opportunities for change, there are important roles to be played by advocacy groups internationally. Cancer 2011;117(10 suppl):2245–9. © 2011 American Cancer Society.

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Section: Introductionmentioning

confidence: 99%

Useful synthetic method of polypeptides with well‐defined structure by polymerization of activated urethane derivatives of α‐amino acids

Yamada¹,

Koga²,

Endō³

2012

J. Polym. Sci. A Polym. Chem.

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“…To date, some researchers have reported various useful methods for polypeptide synthesis. Buess et al developed α‐carboxy hydroxamic acids that rearranged into isocyanate carboxylic acids with a potential capability to give corresponding polypeptides . Orgel et al used N, N ′‐carbonyldiimidazole for the polycondensation of α‐amino acids in aqueous solution .…”

Section: Introductionmentioning

confidence: 99%

Phosgene‐free synthesis of polypeptides: Useful synthesis for hydrophobic polypeptides through polycondensation of activated urethane derivatives of α‐amino acids

Yamada

Koga

Sudo

et al. 2013

J. Polym. Sci. Part A: Polym. Chem.

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We report a useful synthetic method of polypeptides using a series of urethane derivative of α‐amino acids (l‐leucine, l‐phenylalanine, l‐valine, l‐alanine, l‐isoleucine, l‐methionine), which are readily synthesized by N‐carbamoylation of tetrabutylammonium salts of α‐amino acids with diphenyl carbonate. Heating these urethane derivatives in N,N‐dimethylacetamide in the presence of n‐butylamine successfully gave the corresponding polypeptides with well‐defined structures through polycondensation with the elimination of phenol and CO2. The matrix‐assisted laser desorption/ionization time‐of‐flight mass spectrometry investigation showed that the resulting polypeptides had an n‐BuNH2‐incorporated initiating end and an amino group at propagating end. These results strongly indicated that primary amines served as an initiator in this polycondensation system. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 3726–3731

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“…However, the high reactivity of NCA sometimes makes its synthesis and isolation rather difficult, and this issue has prompted many researchers to develop alternative methods with using more easily accessible amino acid‐derivatives that can serve as precursors for NCA under the corresponding polymerization conditions. For example, Buess et al, used α‐carboxy hydroxamic acid for polypeptide synthesis 16. By heating under basic conditions, this compound underwent rearrangement into isocyanato carboxylic acid, which was a potential bifunctional monomer capable of giving the corresponding polypeptide.…”

Section: Introductionmentioning

confidence: 99%

“…For example, Buess et al, used a-carboxy hydroxamic acid for polypeptide synthesis. 16 By heating under basic conditions, this compound underwent rearrangement into isocyanato carboxylic acid, which was a potential bifunctional monomer capable of giving the corresponding polypeptide. Orgel et al, reported the application of a-(N-imidazolylcarbonylamino)-carboxylic acids, to the synthesis of cyclic oligopeptides.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of polypeptides from activated urethane derivatives of α‐amino acids

Kamei

Sudo

Nishida

et al. 2008

J. Polym. Sci. A Polym. Chem.

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A series of activated urethane‐type derivatives of α‐amino acids were synthesized and applied to polypeptide synthesis. The urethane used herein, N‐(4‐nitrophenoxycarbonyl)‐α‐amino acids 1, were synthesized by N‐carbamoylation of γ‐benzyl‐L‐glutamate, β‐benzyl‐L‐aspartate, L‐leucine, L‐phenylalanine, and L‐proline, with 4‐nitrophenyl chloroformate. When 1 was dissolved in N,N‐dimethylacetamide (DMAc) and heated at 60 °C, it was smoothly converted into the corresponding polypeptides with releasing 4‐nitrophenol and carbon dioxide. Spectroscopic analyses of the obtained polypeptides revealed that they were comparable with the authentic polypeptides synthesized by the ring‐opening polymerizations of amino acid N‐carboxyanhydrides (NCAs). Besides the successful polycondensations of a series of 1, their polycondensations of 1a and other 1 were also successfully carried out to obtain the corresponding statistic copolypeptides. © 2008 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 46: 2525–2535, 2008

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The Formation of Polypeptides by Rearrangement of α-Carboxy Hydroxamic Acids

Cited by 23 publications

References 0 publications

Useful synthetic method of polypeptides with well‐defined structure by polymerization of activated urethane derivatives of α‐amino acids

Useful synthetic method of polypeptides with well‐defined structure by polymerization of activated urethane derivatives of α‐amino acids

Phosgene‐free synthesis of polypeptides: Useful synthesis for hydrophobic polypeptides through polycondensation of activated urethane derivatives of α‐amino acids

Synthesis of polypeptides from activated urethane derivatives of α‐amino acids

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