N,N′-carbonyldiimidazole-induced peptide formation in aqueous solution

Ehler, Kenneth W.; Orgel, Leslie E.

doi:10.1016/0005-2795(76)90055-6

Cited by 95 publications

(79 citation statements)

References 17 publications

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“…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. [17][18][19][20][21][22] Recently, we have developed newly synthetic route for production of NCA through intramolecular cyclization of N-(phenyloxycarbonyl) amino acids under heating in moderately polar solvents, such as 2-butanone, tetrahydrofuran (THF), and acetonitrile to give the corresponding NCA, without the use and production of any toxic compounds.…”

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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“…Polycondensation of amino acids is possible in solution when monomers are activated using N-carboxyanhydride [65][66][67][68], however sequence specificity is impossible in such a situation. The introduction of a membrane changes the dynamics of the condensation reaction such that hydrophobic amino acids can be joined more efficient (high rates, yields and length of products) on membranes than in solution [69,70].…”

Section: Membranes As Multiphase Reaction Systems and Reaction Scaffoldsmentioning

confidence: 99%

Primitive Membrane Formation, Characteristics and Roles in the Emergent Properties of a Protocell

Maurer

Monnard

2011

Entropy

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All contemporary living cells are composed of a collection of self-assembled molecular elements that by themselves are non-living but through the creation of a network exhibit the emergent properties of self-maintenance, self-reproduction, and evolution. This short review deals with the on-going research that aims at either understanding how life emerged on the early Earth or creating artificial cells assembled from a collection of small chemicals. In particular, this article focuses on the work carried out to investigate how self-assembled compartments, such as amphiphile and lipid vesicles, contribute to the emergent properties as part of a greater system.

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“…Carbonyldiimidazole (CDI), in aqueous solution, brings about the oligomerization of amino acids and N-monoalkylated amino acids including glycine, sarcosine, alanine, phenylalanine and histidine (Ehler and Orgel, 1976;Ehler et al, 1977).…”

Section: Introductionmentioning

confidence: 99%

Catalysis of the oligomerization of O-phospho-serine, aspartic acid, or glutamic acid by cationic micelles

Böhler

Hill

Orgel

1996

Origins Life Evol Biosphere

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Abstract. Treatment of relatively concentrated aqueous solutions of O-phospho-serine (50 mM), aspartic acid (100 mM) or glutamic acid (100 mM) with carbonyldiimidazole leads to the formation of an activated intermediate that oligomerizes efficiently. When the concentration of amino acid is reduced tenfold, few long oligomers can be detected. Positively-charged cetyltrimethyl ammonium bromide micelles concentrate the negatively-charged activated intermediates of the amino acids at their surfaces and catalyze efficient oligomerization even from dilute solutions.

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N,N′-carbonyldiimidazole-induced peptide formation in aqueous solution

Cited by 95 publications

References 17 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

Primitive Membrane Formation, Characteristics and Roles in the Emergent Properties of a Protocell

Catalysis of the oligomerization of O-phospho-serine, aspartic acid, or glutamic acid by cationic micelles

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