Cu(II)-promoted ortho alkynylation of arenes and heteroarenes with terminal alkynes has been developed to prepare aryl alkynes. A variety of arenes and terminal alkynes bearing different substituents are compatible with this reaction, thus providing an alternative disconnection to Sonogashira coupling.

Cu(II)-mediated ortho C-H alkynylation of (hetero)arenes with terminal alkynes.

In the search for synthetic mimics of protein secondary structures relevant to the mediation of protein–protein interactions, we have synthesized a series of tetrasubstituted diphenylacetylenes that display ?-sheet structures in two directions. Extensive X-ray crystallographic and NMR solution phase studies are consistent with these proteomimetics adopting sheet structures, displaying both hydrophobic and hydrophilic amino acid side chains.

Diphenylacetylene‐Linked Peptide Strands Induce Bidirectional β‐Sheet Formation

The high-affinity immunoglobulin E receptor as pharmacological target

Treatment of N-alkoxyamides with NBS in toluene was found to conveniently afford the corresponding carboxylic esters, including those bearing a bulky or long-chain substituent, in satisfactory to excellent yields. This approach not only represents a convenient and economic approach to a direct transformation of an alkoxyamide moiety into the carboxylic ester functional group, via oxidative homocoupling and the subsequent thermal denitrogenation, but also facilitates the synthesis of sterically hindered carboxylic esters.

Direct conversion of N-alkoxyamides to carboxylic esters through tandem NBS-mediated oxidative homocoupling and thermal denitrogenation.

Conformationally Locked Tolans, β-Sheet Structures, and Photophysical Properties.

The disruption of the human immunolobulin E–high affinity receptor I (IgE–FceRI) protein–protein interaction (PPI) is a validated strategy for the development of anti asthma therapeutics Here, we describe the synthesis of an array of conformationally constrained cyclic peptides based on an epitope of the A–B loop within the Ce3 domain of IgE The peptides contain various tolan (ie, 1,2-biarylethyne) amino acids and their fully and partially hydrogenated congeners as conformational constraints Modest antagonist activity (IC50 ∼660 μM) is displayed by the peptide containing a 2,2′-tolan, which is the one predicted by molecular modeling to best mimic the conformation of the native A–B loop epitope in IgE

Synthesis and incorporation into cyclic peptides of tolan amino acids and their hydrogenated congeners: construction of an array of A-B-loop mimetics of the Cε3 domain of human IgE.

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Synthesis and incorporation into cyclic peptides of tolan amino acids and their hydrogenated congeners: construction of an array of A-B-loop mimetics of the Cε3 domain of human IgE.