Simple and Rapid Synthesis of Branched Peptides through Microwave-Assisted On-Bead Ligation

Vijayasimha Molakaseema; Anand Selvaraj; Hui-Ting Chen; Yen-Wei Chen; Yi-Chang Liu; Chai-Lin Kao

doi:10.1021/acs.joc.1c01455

Simple and Rapid Synthesis of Branched Peptides through Microwave-Assisted On-Bead Ligation

J Org Chem. 2022 Jan 7;87(1):1-9. doi: 10.1021/acs.joc.1c01455. Epub 2021 Oct 22.

Authors

Vijayasimha Molakaseema¹, Anand Selvaraj¹, Hui-Ting Chen^{2

3}, Yen-Wei Chen¹, Yi-Chang Liu^{4

5}, Chai-Lin Kao^{1

6

7

8}

Affiliations

¹ Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan.
² Department of Fragrance and Cosmetic Science, Kaohsiung Medical University, Kaohsiung 807, Taiwan.
³ Department of Pharmacy, National Yang Ming Chiao Tung University, Taipei 112, Taiwan.
⁴ Faculty of Medicine, College of Medicine, Kaohsiung Medical University, Kaohsiung 807, Taiwan.
⁵ Division of Hematology-Oncology, Department of Internal Medicine, Kaohsiung Medical University Hospital, Kaohsiung 807, Taiwan.
⁶ Department of Medical Research, Kaohsiung Medical University Hospital, Kaohsiung 807, Taiwan.
⁷ Department of Chemistry, National Sun Yat-sen University, Kaohsiung 80424, Taiwan.
⁸ College of Professional Studies, National Pingtung University of Science and Technology, Pingtung 912, Taiwan.

PMID: 34677067
DOI: 10.1021/acs.joc.1c01455

Abstract

A rapid on-bead convergent method for preparing branched peptides was reported. Linear peptides were prepared on Dbz resin and ligated various branched cores, including lysine dendrons and other dendritic compounds. Alongside microwave irradiation, <1.5 equiv of peptides is sufficient to afford 50-65% yields of pure branched peptides without chromatographic purification. Remarkably, the desired compounds were prepared within hours.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Microwaves*
Peptides*

Substances

Peptides