| Abstract
| - Self-assembled monolayers (SAMs) of alkanethiols (ATs) on gold can be used to fabricate surfaces for nanoscienceand biology. The chemical structure of the interface can be tailored simply by modifying the AT headgroup. Tostreamline access to different precursor ATs, we developed a general solid-phase synthetic route. A key feature ofthis route is the use of a modified resin containing an AT linker (“AT resin”) because it minimizes purification steps.The precursor to the AT resin was prepared in five steps, and all of the synthetic intermediates are stable solids thatcan be purified by crystallization. Accordingly, the AT resin can be prepared on a multigram scale. The utility of theAT resin was evaluated by using it to generate a variety of ATs. For example, ATs presenting different types ofintegrin-binding ligands (linear and cyclic RGD derivatives) were prepared and used to form arrays of SAMs thatsupport cell adhesion. Additionally, the AT resin also provides a starting point for the synthesis of ATs presentingreactive groups (e.g., an amine-reactive AT or a maleimide-containing alkanedisulfide) or protein immobilization tags(e.g., biotin-AT). Thus, our synthetic strategy provides a convenient and flexible means for the synthesis of thenecessary building blocks for custom SAMs and SAM arrays.
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