92507-06-7

Upstream product

• 2448-45-5 Cbz-D-Phe 
• 769922-77-2 (S)-benzyl (1-(1H-benzo[d][1,2,3]triazol-1-yl)-1-oxo-3-phenylpropan-2-yl)carbamate 
• 3397-32-8 N-(benzyloxycarbonyl)-phenylalanine-N-hydroxysuccinimide ester 
• 1161-13-3 N-Cbz-L-Phe 

Downstream Products

• 1177817-58-1 benzyloxycarbonyl-Phe-3,4-difluoroanilide 
• 927191-07-9 N^α-benzyloxycarbonyl-N'-(4-cyanophenyl)-L-phenylalaninamide 

Relevant academic research and scientific papers

Ynamide-Mediated Thiopeptide Synthesis

Exploration of the full potential of thioamide substitution as a tool in the chemical biology of peptides and proteins has been hampered by insufficient synthetic strategies for the site-specific introduction of a thioamide bond into a peptide backbone. A novel ynamide-mediated two-step strategy for thiopeptide bond formation with readily available monothiocarboxylic acids as thioacyl donors is described. The α-thioacyloxyenamide intermediates formed from the ynamides and monothiocarboxylic acids can be purified, characterized, and stored. The balance between their activity and stability enables them to act as effective thioacylating reagents to afford thiopeptide bonds under mild reaction conditions. Amino acid functional groups such as OH, CONH2, and indole NH groups need not be protected during thiopeptide synthesis. The modular nature of this strategy enables the site-specific incorporation of a thioamide bond into peptide backbones in both solution and the solid phase.

A Facile Synthesis of Thioacids from N -Acylbenzotriazoles

Protected amino/peptide thioacids have been synthesized in pure form in excellent yields and with retention of chirality by using protected aminoacyl- and peptidoylbenzotriazoles as active intermediates. Georg Thieme Verlag Stuttgart, New York.

Facile N-urethane-protected α-amino/peptide thioacid preparation using EDC and Na2S

We report herein an efficient protocol for the synthesis of N-urethane-protected α-amino/peptide thioacids from their corresponding acids mediated by EDC and Na2S. The fast reaction under mild conditions enabled the process to be completed in shorter duration with good yield circumventing column purification. The chemistry is compatible with a wide variety of urethane protecting groups, side-chain functionalities, and sterically hindered amino -acids. Georg Thieme Verlag Stuttgart. New York.

A novel acid-catalyzed isomerization of Aib-containing thiodipeptides

The use of amino thioacids in the 'azirine/oxazolone method' led to completely epimerized Aib-containing endothiodipeptides (Aib=2- aminoisobutyric acid). It could be established that the epimerization occurred during the acidic hydrolysis of the primaril

Reductive Acylation of α-Keto Azides Derived from L-Amino Acids using N-Protected L-Aminothiocarboxylic S-Acids

Several homochiral N-protected α-aminothiocarboxylic S-acids have been synthesised from natural amino acids and used for reductive acylation of homochiral α,α'-amino keto azides, also derived from natural amino acids.