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

Srinivasa Rao Manne; Anamika Sharma; Andrius Sazonovas; Ayman El-Faham; Beatriz G de la Torre; Fernando Albericio

doi:10.1021/acsomega.1c06342

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

ACS Omega. 2022 Feb 9;7(7):6007-6023. doi: 10.1021/acsomega.1c06342. eCollection 2022 Feb 22.

Authors

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}

Affiliations

¹ Peptide Science Laboratory, School of Chemistry and Physics, University of KwaZulu-Natal, Westville, Durban 4000, South Africa.
² KwaZulu-Natal Research Innovation and Sequencing Platform (KRISP), School of Laboratory Medicine and Medical Sciences, College of Health Sciences, University of KwaZulu-Natal, Durban 4041, South Africa.
³ Department of Chemistry, Prayoga Institute of Education Research (PIER), Bangalore 560082, India.
⁴ Advanced Chemistry Development, Inc. (ACD/Labs), 8 King Street East, Suite 107, Toronto, Ontario M5C 1B5, Canada.
⁵ Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, Alexandria 21321, Egypt.
⁶ Institute for Advanced Chemistry of Catalonia (IQAC-CSIC), Jordi Girona 18-26, 08034 Barcelona, Spain.
⁷ CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, and Department of Organic Chemistry, University of Barcelona, Martí i Franqués 1-11, 08028 Barcelona, Spain.

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.