212612-58-3Relevant academic research and scientific papers
Building constrained peptidomimetics: A convenient approach to 3-phenyl-5-vinyl substituted proline derivatives
Duan, Shengquan,Moeller, Kevin D
, p. 6407 - 6415 (2007/10/03)
An approach to the synthesis of 3-phenyl-5-vinyl substituted prolines starting from readily available 2,3-disubstituted pentenoic acid derivatives is reported. The route converts the pentenoic acid derived starting materials into cyclic N-acyliminium ion precursors with the use of a hydroboration-Swern oxidation sequence. This overall transformation worked best when the initial alkylborane product was treated sequentially with excess MCPBA and then acetone prior to the Swern oxidation. In this way, a 70% yield of the desired N-acyliminium ion precursor could be obtained. Once in hand, the cyclic N-acyliminium ion precursor was used to make the desired 3-phenyl-5-vinyl substituted prolines.
Conformationally constrained substance P analogues: The total synthesis of a constrained peptidomimetic for the Phe7-Phe8 region
Tong, Yunsong,Fobian, Yvette M.,Wu, Meiye,Boyd, Norman D.,Moeller, Kevin D.
, p. 2484 - 2493 (2007/10/03)
A lactam-based peptidomimetic for the Phe7-Phe8 region of substance P has been synthesized. The synthesis used an anodic amide oxidation to selectively functionalize the C5-position of a 3-pheylproline derivative. The resulting proline derivative was coupled to a Cbz-protected phenylalanine, and an intramolecular reductive amination strategy used to convert the coupled material into a bicyclic piperazinone ring skeleton. The net result was a dipeptide building block that imbedded one of two proposed receptor bound conformations for the Phe7-Phe8 region of substance P into a bicyclic ring skeleton. The building block was then converted into a constrained substance P analogue with the use of solid-phase peptide synthesis. A similar intramolecular reductive amination strategy was used to synthesize a substance P analogue having only Phe7 constrained, and the original 3-phenylproline was converted into a substance P analogue having only Phe8 constrained. All of the analogues were examined for their ability to displace substance P from its NK-1 receptor.
Conformational probes for elucidating the nature of substance P binding to the NK1 receptor: Initial efforts to map the Phe7-Phe8 region
Tong, Yunsong,Fobian, Yvette M.,Wu, Meiye,Boyd, Norman D.,Moeller, Kevin D.
, p. 1679 - 1682 (2007/10/03)
Three substance P analogs with conformation constraints in the Phe7- Phe8 region have been prepared in connection with an effort to differentiate two families of potential conformations for the binding of substance P to its NK1
