746586-45-8

Upstream product

• 63-91-2 L-phenylalanine 
• 7401-37-8 benzylsulfanylacetaldehyde 
• 91905-68-9 [(2,2-diethoxyethyl)sulfanylmethyl]benzene 
• 100-53-8 phenylmethanethiol 

Downstream Products

• 1026177-01-4 (S)-2-[(2-Benzylsulfanyl-ethyl)-trimethylsilanyl-amino]-3-phenyl-propionic acid 

Relevant academic research and scientific papers

Building units for N-backbone cyclic peptides. Part 4. Synthesis of protected Nα-functionalized alkyl amino acids by reductive alkylation of natural amino acids

A new method for the synthesis of protected Nα-(ω-Y-alkyl) amino acids (Y is a thio, amino or carboxy group) and related compounds by reductive alkylation of natural amino acids is reported. These new amino acids serve as building units for the synthesis of backbone-cyclic peptides. They are orthogonally protected at the α-amino position by butoxycarbonyl (Boc) or 9-fluorenylmethoxycarbonyl (Fmoc), using trimethylsilyl temporary protection, to allow for their incorporation into peptides by solid phase peptide synthesis.

Building units for N-backbone cyclic peptides. 2. Synthesis of protected N-(ω-thioalkylene) amino acids and their incorporation into dipeptide units

A new family of amino acids which contain an ω-thioalkylene group on the N(α)-amino nitrogen was synthesized by alkylation of ω-thioalkylamines with triflates of α-hydroxy acids. The reaction proceeded with inversion of configuration yielding optically pure products. The N(α)-(ω-thioalkylene)amino acids were orthogonally protected to allow their incorporation into peptides by solid-phase peptide synthesis (SPPS) methodology. In addition some of these new protected N(α)-(ω-thioalkylene)amino acids were incorporated into dipeptides by 'solution' techniques.