Serinol-Based Versatile Disulfide-Reducing Reagent

Babita Kushwaha; Sinenhlanhla N Mthembu; Anamika Sharma; Fernando Albericio; Beatriz G de la Torre

doi:10.3390/molecules28145489

Serinol-Based Versatile Disulfide-Reducing Reagent

Molecules. 2023 Jul 18;28(14):5489. doi: 10.3390/molecules28145489.

Authors

Babita Kushwaha¹, Sinenhlanhla N Mthembu^{1

2}, Anamika Sharma^{1

2

3}, Fernando Albericio^{2

4}, Beatriz G de la Torre¹

Affiliations

¹ 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.
² Peptide Science Laboratory, School of Chemistry and Physics, University of KwaZulu-Natal, Durban 4000, South Africa.
³ Department of Natural Products and Medicinal Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.
⁴ CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Department of Organic Chemistry, University of Barcelona, 08028 Barcelona, Spain.

Abstract

Here, we report the synthesis of disulfide-reducing agents 2-(dibenzylamino) propane-1,3-dithiol (DPDT) and 2-(dibenzylamino)-2-methylpropane-1,3-dithiol (DMPDT) from serinol and methyl serinol, respectively. DPDT was found to show greater stability than DMPDT. Hence, the effectiveness of DPDT as a reducing agent was evaluated in both liquid and solid phases. The reducing capacity of this agent was comparable to that of DTT.

Keywords: cysteine; disulfide-reducing agents; dithiols; monothiols; phosphines.

Grants and funding

This work was partially funded by the National Research Foundation (NRF) (Blue Sky’s Research Program # 120386).