30735-47-8

Upstream product

• 1145-80-8 N-(benzyloxycarbonyl)-L-serine 
• 6456-74-2 Glycine tert-butyl ester 
• 501-53-1 benzyl chloroformate 
• 27532-96-3 glycine tert-butyl ester hydrochloride 

Downstream Products

• 943531-09-7 N-benzyloxycarbonyl-O-(p-nitrophenoxycarbonyl)-L-serinylglycine tert-butyl ester 
• 943531-06-4 N-benzyloxycarbonyl-O-(p-nitrophenoxycarbonyl)-L-serinylglycine 
• 132866-45-6 N-Benzyloxycarbonyl-L-seryl(O-tert-butyl)-glycine tert-butyl ester 

Relevant academic research and scientific papers

Diboronic Acid Anhydride-Catalyzed Direct Peptide Bond Formation Enabled by Hydroxy-Directed Dehydrative Condensation

We report the catalytic direct peptide bond formations via dehydrative condensation of β-hydroxy-α-amino acids, affording the serine, threonine, or β-hydroxyvaline-derived peptides in high to excellent yields with high functional group tolerance, minimum epimerization, and excellent chemoselectivity. The key to the success of these atom-economical transformations is the use of diboronic acid anhydride catalyst for the hydroxy-directed reactions.

Acyl transfer from carboxylate, carbonate, and thiocarbonate esters to enzymatic and nonenzymatic thiolates

Transglutaminases (EC 2.3.2.13) (TGases) catalyze calcium-dependent acyl transfer reactions between peptide-bound glutamine residues as acyl donors and peptide-bound lysine residues as acyl acceptors, resulting in the formation of intermolecular ε-(γ-glutamyl)lysine crosslinks. The mechanistic details of its "ping-pong" transamidation reaction remain unknown. In particular, few studies have been published probing the nucleophilicity of TGase using acyl-donor substrates of varied electrophilicity. Herein we report the synthesis of activated esters of carbonates, carbamates, and thiocarbonates and their reactions with simple thiols, as a nonenzymatic point of reference, and with the catalytic cysteine residue of guinea pig liver TGase. Our kinetic results show that the simple substitution of a side chain methylene unit by oxygen or sulphur had a surprising effect on both substrate affinity and acylation reactivity. Furthermore, they provide unexpected insight into the importance of a side chain heteroatom for conferring affinity for tissue TGase as well as revealing an interesting class of irreversible inhibitors.

Enzymatic protecting group techniques for glyco- And phosphopeptide chemistry: Synthesis of a glycophosphopeptide from human serum response factor

The covalent modification of proteins by phosphorylation and by glycosylation with GlcNAc residues are important regulatory processes which mediate biological signal transduction. For the study of such biological phenomena in molecular detail characterist