Synthesis of a Biotin-Conjugated Linker On a Flexible Heteroarotinoid

Abstract

The objective of this study is to synthesize E15 with a biotin-conjugated linker on a methyl moiety in order to isolate specific Flexible Heteroarotinoid (Flex-Het) binding partners in Staphylococcus aureus (ATCC 43300). Flex-Hets are compounds composed of a 4-nitrophenyl group, a linker region, and an aryl ring containing an R group. E15, a Flex-Het containing a methyl R group and a thiourea linker region, has been shown to significantly inhibit the growth of Staphylococcus aureus (ATCC 43300). The reagents used to synthesize E15 are m-toluidine and 4-nitrophenyl isothiocyanate. The amino component on m-toluidine is converted to an amide to protect it while a leaving group is attached to the methyl moiety. Following this, the amide is converted back to an amino group. E15 is synthesized at room temperature by reacting m-toluidine with 4-nitrophenyl isothiocyanate for 24 hours, followed by recrystallization. The biotin-conjugated linker replaces the leaving group on E15, and the product is recrystallized and evaluated by nuclear magnetic resonance.