α‐Sila‐Dipeptides: Synthesis and Characterization

Abstract

The first two a-sila-dipeptides, 7 and cyclo-siladipeptide 8,w ere synthesized and characterized by several methods,i ncluding X-rayc rystallography.B ulkyt -BuMe 2 Si substituents provides ome kinetic stabilization to the synthesized molecules. 7 and 8 are the first examples of a" Si for C switch"inthe central a-position of an amino acid or apeptide, in whichsilicon is bonded to both the amino and the carbonyl groups.

On the Potential of Silicon as a Building Block for Life

“…Silicon provides the basis for diverse chemical function when combined with other atoms (other than carbon). Several examples include Si-S-bond-containing silicon analogues of thiols (thiosilanes) [42][43][44] and Si-N-bond-containing α-sila-amino acids [45]. Dynamic, highly polarized silicon systems, where rapid, reversible chemistry occurs, are also known [46].…”

“…In some cases, the silicon-containing group is incorporated as a side chain substituent, in peptide-like backbone-containing molecules (e.g., in silanediols). Only very recently, the silicon atom been incorporated at the central α-position of an amino acid (7, 8) in a peptide chain forming short silicon-based peptides such as (7) [45]. Synthesis of α-sila-peptides (7) further exemplifies the potential for silicon as a heteroatom in the context of aqueous biochemistry (see Section 4.1).…”