390424-29-0

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 38739-13-8 (2S)-2-amino-3-(3-bromo-4-hydroxyphenyl)propanoic acid 
• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 113311-28-7 (S)-N-Boc-3-bromotyrosine 

Downstream Products

• 390424-30-3 Di-N-Boc-amino-psammaplin A 

Relevant academic research and scientific papers

Combinatorial synthesis through disulfide exchange: Discovery of potent psammaplin A type antibacterial agents active against methicillin-resistant Staphylococcus aureus (MRSA)

Psammaplin A is a symmetrical bromotyrosine-derived disulfide natural product isolated from the Psammaplysilla sponge, which exhibits in vitro antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA). Inspired by the structure of this marine natural product, a combinatorial scrambling strategy for the construction of heterodimeric disulfide analogues was developed and applied to the construction of a 3828-membered library starting from 88 homodimeric disulfides. These psammaplin A analogues were screened directly against various gram positive bacterial strains leading to the discovery of a series of potent antibacterial agents active against methicillin-resistant Staphylococcus aureus (MRSA). Among the most active leads derived from these studies are compounds 104, 105, 113, 115, 123, and 128. The present, catalytically-induced, disulfide exchange strategy may be extendable to other types of building blocks bearing thiol groups facilitating the construction of diverse discovery-oriented combinatorial libraries.