Unwanted hydrolysis or α/β-peptide bond formation: how long should the rate-limiting coupling step take?

Parallel to the amide bond formation, the hydrolysis of the active esters of α/β-amino acids, as an unwanted side reaction limiting coupling efficacy, is studied.

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Ab initio study of catalyzed and uncatalyzed amide bond formation as a model for peptide bond formation: Ammonia-Glycine reactions

Journal of Computational Chemistry ◽

10.1002/jcc.540040402 ◽

1983 ◽

Vol 4 (4) ◽

pp. 449-460 ◽

Cited By ~ 9

Author(s):

Tetsuro Oie ◽

Gilda H. Loew ◽

Stanley K. Burt ◽

Robert D. Macelroy

Keyword(s):

Ab Initio ◽

Bond Formation ◽

Peptide Bond ◽

Amide Bond ◽

Ab Initio Study ◽

Peptide Bond Formation ◽

Amide Bond Formation

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Ab initio study of catalyzed and uncatalyzed amide bond formation as a model for peptide bond formation: Ammonia-formic acid and ammonia-glycine reactions

International Journal of Quantum Chemistry ◽

10.1002/qua.560220722 ◽

2009 ◽

Vol 22 (S9) ◽

pp. 223-245 ◽

Cited By ~ 2

Author(s):

Tetsuro Oie ◽

Gilda H. Loew ◽

Stanley K. Burt ◽

J. Stephen Binkley ◽

Robert D. MacElroy

Keyword(s):

Formic Acid ◽

Ab Initio ◽

Bond Formation ◽

Peptide Bond ◽

Amide Bond ◽

Ab Initio Study ◽

Peptide Bond Formation ◽

Amide Bond Formation

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Faculty Opinions recommendation of An induced-fit mechanism to promote peptide bond formation and exclude hydrolysis of peptidyl-tRNA.

Faculty Opinions – Post-Publication Peer Review of the Biomedical Literature ◽

10.3410/f.1029397.349450 ◽

2005 ◽

Author(s):

Andrea Barta

Keyword(s):

Bond Formation ◽

Peptide Bond ◽

Peptide Bond Formation ◽

Induced Fit ◽

Hydrolysis Of

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ChemInform Abstract: Peptide-Bond Formation with C-Terminal α,α-Disubstituted α-Amino Acids via Intermediate Oxazol-5(4H)-ones.

Chemischer Informationsdienst ◽

10.1002/chin.198646320 ◽

1986 ◽

Vol 17 (46) ◽

Author(s):

P. WIPF ◽

H. HEIMGARTNER

Keyword(s):

Amino Acids ◽

Bond Formation ◽

Peptide Bond ◽

Peptide Bond Formation

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An induced-fit mechanism to promote peptide bond formation and exclude hydrolysis of peptidyl-tRNA

Structural Insights into Gene Expression and Protein Synthesis - Series in Structural Biology ◽

10.1142/9789811215865_0065 ◽

2020 ◽

pp. 552-556

Author(s):

T. Martin Schmeing ◽

Kevin S. Huang ◽

Scott A. Strobel ◽

Thomas A. Steitz

Keyword(s):

Bond Formation ◽

Peptide Bond ◽

Peptide Bond Formation ◽

Induced Fit ◽

Hydrolysis Of

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Facile Amide Bond Formation From Esters of Amino Acids and Peptides Catalyzed by Alkaline Protease in Anhydroustert-Butyl Alcohol Using Ammonium Chloride/Triethylamine as a Source of Nucleophilic Ammonia

Synthesis ◽

10.1055/s-1993-25955 ◽

1993 ◽

Vol 1993 (09) ◽

pp. 858-860 ◽

Cited By ~ 15

Author(s):

Shui-Tein Chen ◽

Ming-Kuei Jang ◽

Kung-Tsung Wang

Keyword(s):

Amino Acids ◽

Ammonium Chloride ◽

Alkaline Protease ◽

Bond Formation ◽

Butyl Alcohol ◽

Amide Bond ◽

Amide Bond Formation

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ChemInform Abstract: Facile Amide Bond Formation from Esters of Amino Acids and Peptides, e. g. (S)-(I), Catalyzed by Alkaline Protease in Anhydrous tert-Butyl Alcohol Using Ammonium Chloride/Triethylamine as a Source of Nucleophilic Ammonia.

ChemInform ◽

10.1002/chin.199406221 ◽

2010 ◽

Vol 25 (6) ◽

pp. no-no

Author(s):

S.-T. CHEN ◽

M.-K. JANG ◽

K.-T. WANG

Keyword(s):

Amino Acids ◽

Ammonium Chloride ◽

Alkaline Protease ◽

Bond Formation ◽

Butyl Alcohol ◽

Amide Bond ◽

Tert Butyl ◽

Amide Bond Formation ◽

Tert Butyl Alcohol

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A simple and greener approach for the amide bond formation employing FeCl3 as a catalyst

New Journal of Chemistry ◽

10.1039/c5nj01047k ◽

2015 ◽

Vol 39 (10) ◽

pp. 7746-7749 ◽

Cited By ~ 12

Author(s):

Basavaprabhu Basavaprabhu ◽

Krishnamurthy Muniyappa ◽

Nageswara Rao Panguluri ◽

Panduranga Veladi ◽

Vommina V. Sureshbabu

Keyword(s):

Amino Acids ◽

Bond Formation ◽

Amide Bond ◽

Bromoacetic Acid ◽

Amide Bond Formation ◽

Glacial Acoh ◽

Sterically Hindered

A protocol employing FeCl3 in the presence of glacial AcOH is described for the less nucleophilic aniline and its variants, bromoacetic acid and sterically hindered amino acids.

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