75779-22-5

Upstream product

• 42854-62-6 L-alanine benzyl ester p-toluenesulfonate 
• 3190-70-3 L-leucine N-carboxyanhydride 
• 100-39-0 benzyl bromide 
• 66450-17-7 Boc-Leu-HONB 
• 126400-95-1 N-(tert-butoxycarbonyl)-L-alanine benzyl ester 
• 17831-01-5 H-Ala-OBzl 
• 13139-15-6 N-tert-butoxycarbonyl-L-leucine 
• 66415-01-8 N-((tert-butoxycarbonyl)-L-leucyl)-L-alanine benzyl ester 
• 17664-94-7 N-(benzyloxycarbonyl)-L-leucyl-L-alanine phenylmethyl ester 

Downstream Products

• 7298-84-2 Leu-Ala 

Relevant academic research and scientific papers

Design criteria for minimalist mimics of protein-protein interface segments

Small molecules that can interrupt or inhibit protein-protein interactions (PPIs) are valuable as probes in chemical biology and medicinal chemistry, but they are also notoriously difficult to develop. Design of non-peptidic small molecules that mimic ami

MACROCYCLIZATION OF PEPTIDOMIMETICS

The invention provides an improved method of macrocyclization of peptidomimetics, as measured by isolated yields and product distribution, which comprises substitution of one or more of the backbone amide C=O bonds with a turn-inducing motif. The method is general with enhancements seen across a range of ring sizes (e.g. tri-, tetra-, penta- and hexapeptides). Specifically, the invention provides a peptidomimetic macrocycle comprising a carbonyl bioisosteric turn-inducing element having the structure: (I) wherein X is a heteroatom; and wherein R1 to R6 are each independently selected from alkyl, aryl, heteroaryl and H.

Application of a unique automated synthesis system for solution-phase peptide synthesis

An automated synthesis system, which is suitable for repetitive syntheses using similar reaction procedures, was used to synthesize systematically a library of all possible dipeptides (25) and tripeptides (125) from 5 protected amino acids. The apparatus has also been applied to the automated synthesis of 10 fragment tripeptide derivatives that are constituents of the hormone PACAP-27. The measured molecular optical rotation values of the library of 125 tripeptides were found to correlate well with calculated values obtained by summation of the molecular optical rotation values for the constituent amino acids.

The Steric Hindrance of the Stepwise Reaction of N-Carboxy α-Amino Acid Anhydride with the α-Amino Acid Ester

The mechanisms of the reactions of 4-alkyloxazolidinediones (1) (N-carboxy α-amino acid anhydrides(NCAs)) with α-amino acid benzyl ester p-toluenesulfonates (2) were investigated in acetonitrile containing triethylamine at low and room temperatures.Two types of reactions were observed: (1) the polymerization of NCAs was initiated with a small amount of 2 to produce polypeptides (6), and (2) the dipeptide benzyl esters (4) were produced by the stepwise reaction of NCAs with the esters.Both the polymerization and the dipeptide formation (1+2) seemed to be initiated by the nucleophilic attack of the amino group of the ester on the C-5 carbon of NCAs.The polymerization proceeded when the side chains of the amino acid esters (R2) were more bulky than those of the NCAs (R1).On the contrary, dipeptide esters were produced when the side chains of the NCAs (R1) were more bulky than those of the esters (R2).