60058-40-4

Upstream product

• 74-89-5 methylamine 
• 583-47-1 4-benzyl-oxazolidine-2,5-dione 
• 5619-07-8 methyl 2-amino-3-phenylpropanoate hydrochloride 
• 3588-57-6 Z-DL-Phe-OH 
• 15028-44-1 DL-phenylalanine methyl ester 
• 150-30-1 Phenylalanine 

Downstream Products

• 77920-72-0 N-pyruvoyl-N'-methylphenylalanineamide 
• 52785-21-4 1-methyl-3-benzyl-6-methylene-3,5-dioxopiperazine 
• 1290605-84-3 tert-butyl 3-[[[1-benzyl2-(methylamino)-2-oxoethyl]amino]carbonyl]-5-methylhexanoate 

Relevant academic research and scientific papers

Glycine radicals in the gas phase

2-Glycyl radical (1), 2-glycyl methyl ester (2), and 2-glycyl N-methylamide radicals (3) were generated in the gas phase by collisional neutralization of the corresponding cations and studied by neutralization-reionization (NR) mass spectrometry and ab in

Multi-Institution Research and Education Collaboration Identifies New Antimicrobial Compounds

New antibiotics are urgently needed to address increasing rates of multidrug resistant infections. Seventy-six diversely functionalized compounds, comprising five structural scaffolds, were synthesized and tested for their ability to inhibit microbial growth. Twenty-six compounds showed activity in the primary phenotypic screen at the Community for Open Antimicrobial Drug Discovery (CO-ADD). Follow-up testing of active molecules confirmed that two unnatural dipeptides inhibit the growth of Cryptococcus neoformans with a minimum inhibitory concentration (MIC) ≤ 8 μg/mL. Syntheses were carried out by undergraduate students at five schools implementing Distributed Drug Discovery (D3) programs. This report showcases that a collaborative research and educational process is a powerful approach to discover new molecules inhibiting microbial growth. Educational gains for students engaged in this project are highlighted in parallel to the research advances. Aspects of D3 that contribute to its success, including an emphasis on reproducibility of procedures, are discussed to underscore the power of this approach to solve important research problems and to inform other coupled chemical biology research and teaching endeavors.

Bioinspired Radical Stetter Reaction: Radical Umpolung Enabled by Ion-Pair Photocatalysis

A bioinspired, intermolecular radical Stetter reaction of α-keto acids and aldehydes is disclosed that is contingent on a formal “radical umpolung” concept. Enabled by secondary amine activation, electrostatic recognition ensures that the α-ketocarboxylic acids, which function as latent acyl radicals, are proximal to the in situ generated iminium salts. This photoactive contact ion pair is an electron donor–acceptor (EDA) complex, and undergoes facile single electron transfer (SET) and rapid decarboxylation prior to radical–radical recombination. Importantly, decarbonylation is mitigated by this strategy. The initial computational validation on which the process is predicated matches closely with experiment. Synergising organo- and photocatalysis activation principles finally expands the mechanistic and synthetic scope of the classic Stetter reaction to include α,β-unsaturated aldehydes as acceptors.

Isomer differentiation via collision-induced dissociation: The case of protonated a-, β2- and β3-phenylalanines and their derivatives

A combination of electrospray ionisation (ESI), multistage and high-resolution mass spectrometry experiments is used to examine the gas-phase fragmentation reactions of the three isomeric phenylalanine derivatives, a-phenylalanine, b2-phenylalanine and b3-phenylalanine. Under collision-induced dissociation (CID) conditions, each of the protonated phenylalanine isomers fragmented differently, allowing for differentiation. For example, protonated b3-phenylalanine fragments almost exclusively via the loss of NH3, only b2-phenylalanine via the loss of H2O, while a- and b2- phenylalanine fragment mainly via the combined losses of H2ORCO. Density functional theory (DFT) calculations were performed to examine the competition between NH3 loss and the combined losses of H2O and CO for each of the protonated phenylalanine isomers. Three potential NH3 loss pathways were studied: (i) an aryl-assisted neighbouring group; (ii) 1,2 hydride migration; and (iii) neighbouring group participation by the carboxyl group. Finally, we have shown that isomer differentiation is also possible when CID is performed on the protonated methyl ester and methyl amide derivatives of a-, b2- and b3-phenylalanines.

IRON MODULATORS

Iron modulator compounds of formula (I) are provided for treating amyloidoses wherein R1 is selected from H, C1-6 alkyl, C1-6 alkenyl, C1-6 hydroxyalkyl, C1-6 hydroxyalkenyl, R2 is selected from H, C1-6 alkyl, C1-6 alkenyl, C1-6 hydroxyalkyl, C1-6 hydroxyalkenyl and C6-10 aralykyl in which the aryl group of the aralkyl group is optionally substituted by hydroxy, halo or C1-4 alkyl R3 is selected from H, C1-6 alkyl, C1-6 alkenyl and C1-12 acyl; R4 is selected from H and C1-3 alkyl R5, R6 and R7 are independently selected from H, C1-6 alkyl, C3-7 aryl, and C1-10 aralkyl; the alkyl, aryl and aralkyl groups being optionally substituted by one or more halo, hydroxy and nitro groups or R5 and R7 together with the nitrogen atom to which they are bonded form a heterocyclic ring optionally substituted by one or more hydroxyl groups or a pharmaceutically acceptable tautomer, ester or addition salt thereof.

The photochemistry of N-p-toluenesulfonyl peptides: The peptide bond as an electron donor

The scope of photobiological processes that involve absorbers within a protein matrix may be limited by the vulnerability of the peptide group to attack by highly reactive redox centers consequent upon electronic excitation. We have explored the nature of this vulnerability by undertaking comprehensive product analyses of aqueous photolysates of 12 N-p-toluene-sulfonyl peptides with systematically selected structures. The results indicate that degradation includes a major pathway that is initiated by intramolecular electron transfer in which the peptide bond serves as electron donor, and the data support the likelihood' of a relay process in dipeptide derivatives.

Synthesis of dehydroamino acids and didehydrodioxopiperazines and their conversion into α-mercapto-α-amino acid derivatives

A synthesis of α,β-dehydroamino acid derivatives 12 is described, which is of possible general applicability and might be useful for the preparation of peptides which have such a moiety in their sequence.I addition, several didehydrodioxopiperazines (13-1