77935-37-6

Upstream product

• 77443-49-3 (S)-benzyl 2-((S)-2-((tert-butoxycarbonyl)amino)-3-methylbutanamido)-3-methylbutanoate 
• 13734-41-3 t-Boc-L-valine 
• 21760-98-5 L-valine benzyl ester 
• 69936-04-5 (+)-(S)-valyl-(S)-valine methyl ester hydrochloride 
• 138892-09-8 Methyl N--L-valinate 
• 138892-16-7 (S)-2-[(S)-2-(Benzhydrylidene-amino)-3-methyl-butyrylamino]-3-methyl-butyric acid benzyl ester 

Downstream Products

• 99429-50-2 Boc-Val-Val-Val-OBzl 
• 77443-49-3 (S)-benzyl 2-((S)-2-((tert-butoxycarbonyl)amino)-3-methylbutanamido)-3-methylbutanoate 
• 111052-95-0 Boc-Val-Val-Val-Gly-Gly-OBzl 
• 111052-94-9 Z-Gly-Gly-Val-Val-Val-OBzl 

Relevant academic research and scientific papers

Oxygen alkylation of Schiff base derivatives of amino acids

Higher imine esters 1a-h and 7a-b of amino acids and dipeptides are prepared in 68-91% yield by saponification of the benzophenone Schiff base methyl esters 3a-d and 6 using phase-transfer techniques followed by O-alkylation with an alkyl halide. The procedure occurs with retention of configuration at the α-carbon except with phenylglycine derivatives.

Variation in Bitterness Potency When Introducing Gly-Gly Residue into Bitter Peptides

We previously reported that Gly-Gly-Arg-Pro and Arg-Pro-Gly-Gly, the derivatives of a bitter peptide Arg-Pro, had no bitterness although Gly-Arg-Pro and Arg-Pro-Gly had a bitter taste at the same level as that of Arg-Pro.To elucidate the mechanism of elimination of bitterness by the introduction of the Gly-Gly residues, we synthesized Gly-Gly derivatives of other bitter peptides such as Phe-Phe, Val-Val-Val, Arg-Pro-Phe-Phe, and examined the effectiveness of Gly-Gly residues in eliminating bitterness.We suggest that, for Arg-Pro and Val-Val-Val, the Gly-Gly residue might prevent a hydrophobic group from binding to a taste receptor.