537710-06-8

Upstream product

• 4530-20-5 BOC-glycine 
• 106-96-7 propargyl bromide 
• 107-19-7 propargyl alcohol 

Downstream Products

• 183554-08-7 2S-[[(1,1-dimethylethoxy) carbonyl]amino]-N-[2R-hydroxy-3-[[(1,3-benzodioxol-5-yl)sulfonyl](2-methylpropyl)amino]-1S-(phenylmethyl) propyl]pent-4-ynamide 
• 33952-53-3 cyclohexylcarbamoylmethylcarbamic acid t-butyl ester 
• 19811-52-0 Boc-glycine-benzylamide 
• 613675-75-5 tert-butyl N-{[(2-phenylethyl)carbamoyl]methyl}carbamate 
• 64991-29-3 tert-butyl (2S)-2-(2-{[(tert-butoxy)carbonyl]amino}acetamido)-3-phenylpropanoate 

Relevant academic research and scientific papers

In Vivo Gold Complex Catalysis within Live Mice

Metal complex catalysis within biological systems is largely limited to cell and bacterial systems. In this work, a glycoalbumin–AuIII complex was designed and developed that enables organ-specific, localized propargyl ester amidation with nearby proteins within live mice. The targeted reactivity can be imaged through the use of Cy7.5- and TAMRA-linked propargyl ester based fluorescent probes. This targeting system could enable the exploitation of other metal catalysis strategies for biomedical and clinical applications.

Multifunctional polyether grafted dendritic solid supports: Novel class of solvent like high loading hybrid supports for solid phase organic synthesis

Three novel multifunctional polyether grafted dendritic solid supports for organic synthesis were developed via single step, grafting from and hypergrafting strategies. In order to improve both the swelling capacity and loading capacity of conventional resins simultaneously, the hybrid supports were developed by grafting either multivalent linear polymers or dendritic architectures to the conventional resin. The ring opening polymerization of strained cyclic monomers was explored for the development of multivalent polymer grafts on the solid support. The physico-chemical properties of the dendritic solid supports were studied by various characterization techniques and analytical methods. Among the hybrid supports, Het-PG was found to be a novel solvent like high loading solid support. High functional group capacity of 7 mmol g?1 which was introduced via single step approach, increased accessibility of functional sites even at high loading etc. make Het-PG a versatile solid support for organic synthesis. The applicability of dendritic solid support (Het-PG) as a high loading hybrid support for multistep solid phase organic synthesis of small peptides was investigated. The high functional group capacity and increased accessibility of functional sites in Het-PG were exploited for addressing the poor industrial scalability issue of solid phase organic synthesis. A novel approach to solid phase peptide synthesis using solvent like high loading hybrid solid support is presented.

Synthesis and Analysis of Natural-Product-Like Macrocycles by Tandem Oxidation/Oxa-Conjugate Addition Reactions

As traditional small-molecule drug discovery programs focus on a relatively narrow range of chemical space, most human proteins are viewed as unreachable targets. Consequently, there is a strong interest in expanding the chemical space in drug discovery b

2-Benzoylpyridine Ligand Complexation with Gold Critical for Propargyl Ester-Based Protein Labeling

In previously reported work, AuIII complexes coordinated with 2-benzoylpyridine ligand, BPy-Au, were prebound to a protein and used to discover a novel protein-directed labeling approach with propargyl ester functional groups. In this work, further examination discovered that gold catalysts devoid of the 2-benzoylpyridine ligand (e.g., NaAuCl4) had significantly reduced levels of protein labeling. Mechanistic investigations then revealed that BPy-Au and propargyl esters undergo a rare example of C(sp2)?C(sp) aryl–alkynyl cross-coupling, likely through spontaneous reductive elimination. Overall, these observations appear to suggest that BPy-Au-mediated, propargyl ester-based protein labeling acts via an activated ester intermediate, which contributes to our understanding of this process and will aid the expansion/optimization of gold-catalyst usage in future bioconjugation applications, especially in vivo.

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.