64187-26-4

Upstream product

• 107-19-7 propargyl alcohol 
• 1138-80-3 N-(Benzyloxycarbonyl)glycine 
• 106-96-7 propargyl bromide 

Downstream Products

• 291527-34-9 methyl 2-(benzyloxycarbonyl)amino-4-iodopent-4-enoate 
• 109974-62-1 benzyl 2-(hexylamino)-2-oxoethylcarbamate 

Relevant academic research and scientific papers

Cancer cell targeting driven by selective polyamine reactivity with glycine propargyl esters

Rapidly growing cancer cells have increased levels of intracellular polyamines compared to normal, healthy tissues. Based on the selective reactivity of glycine propargyl esters, probes were synthesized that show evidence for selective polyamine reactivit

Propargyl-Assisted Selective Amidation Applied in C-terminal Glycine Peptide Conjugation

Alkyl esters, such as propargyl esters, typically lack the electron-withdrawing inductive effects needed to participate in nucleophilic acyl substitution reactions. Herein, we report an unusual observation in which glycine propargyl ester derivatives displayed selective, base-independent reactivity towards linear alkylamines under mild, metal-free conditions. Through global reaction route mapping (GRRM) modeling calculations, it is predicted that these observations may be governed by factors related to hydrogen-bonding and intermolecular interactions, rather than electron-withdrawing inductive effects. Based on this concept of propargyl-assisted selective amidation, a direct application was made to develop a novel site-specific C-terminal glycine peptide bioconjugation technique as a proof-of-concept, which relies upon the selective reactivity of glycine propargyl esters over that of aspartate and glutamate side-chain-linked propargyl esters.

Preparation and reactions of stannylated amino, acids

Hydrostannations of propargylic glycine esters with the new hydrostannation catalyst [Mo(CO)3(CNtBu)3] (MoBI3) gave rise to α-stannylated allylic esters in good yield and with high regioselectivity. The chelate Claisen rearrangements of these esters allow the syntheses of γ,δ-unsaturated amino acids with a vinylstannane moiety in the side chain. The amino acids obtained can be further modified by cross-coupling with various types of electrophiles.

Antineoplastic agents. 2. Structure-activity studies on N-protected vinyl, 1,2-dibromoethyl, and cyanomethyl esters of several amino acids

Previously reported work on N-protected activated esters of phenylalanine has been extended to include N-protected vinyl, dibromoethyl, and cyanomethyl esters of several other amino acids. These compounds have been synthesized and evaluated in Ehrlich ascites carcinoma, Walker 256 carcinosarcoma, and P388 lymphocytic leukemia tests. Among compounds tested were derivatives of tyrosine, tryptophan, glycine, leucine, proline, aspartic acid, glutamic acid, 4-aminobutyric acid, and 6-aminocaproic acid. Compounds of greatest potential interest from this study are N-carbobenzoxyglycine 1,2-dibromoethyl ester and N-carbobenzoxy-L-leucine 1,2-dibromoethyl ester. Both compounds were highly active in Ehrlich ascites test systems (33 mg/kg/day). The glycine derivative was also active in the Walker 256 test (2.5 mg/kg/day). Values for LD50's in mice were 148 mg/kg (0.37 mmol/kg) and 225 mg/kg (0.50 mmol/kg) for glycine and leucine derivatives, respectively; therefore, these compounds do not appear to be toxic at effective dose levels.