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Literature DB >> 35224362

Understanding OxymaPure as a Peptide Coupling Additive: A Guide to New Oxyma Derivatives.

Srinivasa Rao Manne¹, Anamika Sharma^1,2,3, Andrius Sazonovas⁴, Ayman El-Faham⁵, Beatriz G de la Torre^1,2, Fernando Albericio^1,6,7.

Abstract

An in silico study, using the GALAS algorithm available in ACD/PhysChem Suite, was performed to calculate the pK a(s) of various oximes with potential application as peptide coupling additives. Among the known oximes and predicted structures, OxymaPure is superior based on the pK a values calculated, confirming the results described in the literature and validating this algorithm for further use in that field. Among the nondescribed oximes, based on pK a calculation, ethyl 2-(hydroxyimino)-2-nitroacetate seems to be a potential candidate to be used as an additive during peptide coupling.

Entities: Chemical

Year: 2022 PMID： 35224362 PMCID： PMC8867806 DOI： 10.1021/acsomega.1c06342

Source DB: PubMed Journal: ACS Omega ISSN： 2470-1343

28 in total

1. Synthesis of peptides by aminolysis of nitrophenyl esters.

Authors: M BODANSZKY
Journal: Nature Date: 1955-04-16 Impact factor: 49.962

Review 2. Factors determining the selection of organic reactions by medicinal chemists and the use of these reactions in arrays (small focused libraries).

Authors: Tony W J Cooper; Ian B Campbell; Simon J F Macdonald
Journal: Angew Chem Int Ed Engl Date: 2010-10-25 Impact factor: 15.336

3. Electrophoretic behavior and pKa determination of quinolones with a piperazinyl substituent by capillary zone electrophoresis.

Authors: Ching-Erh Lin; Yan- Deng; Wei-Ssu Liao; Shao-Wen Sun; Wann-Yin Lin; Chia-Chong Chen
Journal: J Chromatogr A Date: 2004-10-08 Impact factor: 4.759

4. Oxyma: an efficient additive for peptide synthesis to replace the benzotriazole-based HOBt and HOAt with a lower risk of explosion.

Authors: Ramon Subirós-Funosas; Rafel Prohens; Rafael Barbas; Ayman El-Faham; Fernando Albericio
Journal: Chemistry Date: 2009-09-21 Impact factor: 5.236

5. Predicting pK_a for Small Molecules on Public and In-house Datasets Using Fast Prediction Methods Combined with Data Fusion.

Authors: Tuomo Kalliokoski; Kai Sinervo
Journal: Mol Inform Date: 2019-05-09 Impact factor: 3.353

Understanding OxymaPure as a Peptide Coupling Additive: A Guide to New Oxyma Derivatives.

1. Synthesis of peptides by aminolysis of nitrophenyl esters.

Review 2. Factors determining the selection of organic reactions by medicinal chemists and the use of these reactions in arrays (small focused libraries).

3. Electrophoretic behavior and pKa determination of quinolones with a piperazinyl substituent by capillary zone electrophoresis.

4. Oxyma: an efficient additive for peptide synthesis to replace the benzotriazole-based HOBt and HOAt with a lower risk of explosion.

5. Predicting pK_a for Small Molecules on Public and In-house Datasets Using Fast Prediction Methods Combined with Data Fusion.

6. Acidity of the amidoxime functional group in aqueous solution: a combined experimental and computational study.

7. PyOxP and PyOxB: the Oxyma-based novel family of phosphonium salts.

8. COMU: a safer and more effective replacement for benzotriazole-based uronium coupling reagents.

9. O-H bond dissociation enthalpies of oximes: a theoretical assessment and experimental implications.

10. Synthesis, characterization and anti-proliferation activities of novel cyano oximino sulfonate esters.

1. Carbodiimide-Mediated Beckmann Rearrangement of Oxyma-B as a Side Reaction in Peptide Synthesis.