875478-11-8

Upstream product

• 867335-87-3 4-[(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-phenylpropanamido]-1-propyne 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 63-91-2 L-phenylalanine 
• 461638-99-3 (S)-tert-butyl (1-oxo-3-phenyl-1-(prop-2-yn-1-ylamino)propan-2-yl)carbamate 
• 35661-40-6 N-Fmoc L-Phe 

Downstream Products

• 1268671-17-5 L-phenylalanine-N-[(1-β-cyclodextrinyl-1H-1,2,3-triazol-4-yl)methylamide] 
• 1268672-11-2 C₁₅H₁₄N₂O₂ 
• 1608889-97-9 C₂₃H₂₇N₅O₃ 
• 1062578-14-6 (S)-5-benzyl-2,2-dimethyl-3-(prop-2-yn-1-yl)imidazolidin-4-one 
• 1358017-45-4 (S)-N-(1-oxo-3-phenyl-1-(prop-2-yn-1-ylamino)propan-2-yl)acrylamide 
• 1449248-82-1 (S)-3-phenyl-2-(phenylamino)-N-(prop-2-ynyl)propanamide 
• 890139-90-9 2-((R)-1-Azidomethyl-2-phenyl-ethylcarbamoyl)-5-{(R)-3-[3-((S)-2-phenyl-1-prop-2-ynylcarbamoyl-ethyl)-ureido]-4-triisopropylsilanyloxy-butyl}-furan-3,4-dicarboxylic acid dimethyl ester 
• 890139-92-1 2-((S)-1-Azidomethyl-2-phenyl-ethylcarbamoyl)-5-{(R)-3-[3-((S)-2-phenyl-1-prop-2-ynylcarbamoyl-ethyl)-ureido]-4-triisopropylsilanyloxy-butyl}-furan-3,4-dicarboxylic acid dimethyl ester 
• 890139-60-3 2-allyl 3,4-dimethyl 5-((R)-3-(3-((S)-1-oxo-3-phenyl-1-(prop-2-ynylamino)propan-2-yl)ureido)-4-(triisopropylsilyloxy)butyl)furan-2,3,4-tricarboxylate 
• 867335-88-4 (R)-2-Azido-4-methyl-pentanoic acid ((S)-2-phenyl-1-prop-2-ynylcarbamoyl-ethyl)-amide 

Relevant academic research and scientific papers

β-Sheet to Helical-Sheet Evolution Induced by Topochemical Polymerization: Cross-α-Amyloid-like Packing in a Pseudoprotein with Gly-Phe-Gly Repeats

Protein-mimics are of great interest for their structure, stability, and properties. We are interested in the synthesis of protein-mimics containing triazole linkages as peptide-bond surrogate by topochemical azide-alkyne cycloaddition (TAAC) polymerization of azide- and alkyne-modified peptides. The rationally designed dipeptide N3-CH2CO-Phe-NHCH2CCH (1) crystallized in a parallel β-sheet arrangement and are head-to-tail aligned in a direction perpendicular to the β-sheet-direction. Upon heating, crystals of 1 underwent single-crystal-to-single-crystal polymerization forming a triazole-linked pseudoprotein with Gly-Phe-Gly repeats. During TAAC polymerization, the pseudoprotein evolved as helical chains. These helical chains are laterally assembled by backbone hydrogen bonding in a direction perpendicular to the helical axis to form helical sheets. This interesting helical-sheet orientation in the crystal resembles the cross-α-amyloids, where α-helices are arranged laterally as sheets.

Synthesis and Reversible Hydration of a Pseudoprotein, a Fully Organic Polymeric Desiccant by Multiple Single-Crystal-to-Single-Crystal Transformations

A diphenylalanine derivative, N3-Phe-Phe-NHCH2CCH, was designed for topochemical azide–alkyne cycloaddition (TAAC) polymerization. This dipeptide adopted β-sheet arrangement as designed, in its crystals, but the azide and alkyne were not fitly aligned for

Chemical probes for competitive profiling of the quorum sensing signal synthase PqsD of Pseudomonas aeruginosa

The human pathogen Pseudomonas aeruginosa uses the pqs quorum sensing system to coordinate the production of its broad spectrum of virulence factors to facilitate colonization and infection of its host. Hereby, the enzyme PqsD is a virulence related quoru

A magnetoclick imidazolidinone nanocatalyst for asymmetric 1,3-dipolar cycloadditions

A 1,3-dipolar azide-alkyne cycloaddition has been used to prepare a magnetic nanoparticle immobilized MacMillan catalyst that catalyzes the enantioselective 1,3-dipolar cycloaddition between nitrones and α,β-unsaturated aldehydes. The catalyst can be recovered and recycled for five consecutive runs without any significant loss in yields and diastereo- and enantioselectivities of the isoxazolidines. Copyright

Using click chemistry to access mono- and ditopic β-cyclodextrin hosts substituted by chiral amino acids

A wide range of chiral mono- and ditopic cyclodextrin-based receptors have been synthesized by CuI-catalyzed azide-alkyne cycloaddition starting from mono-6-azido-β-cyclodextrin and chiral amino acids. Of interest, microwaves proved very efficient to acce

Synthesis and characterisation of hetero-bimetallic organometallic phenylalanine and PNA monomer derivatives

The rational, sequential synthesis of two hetero-bimetallic derivatives of the amino acid phenylalanine and one thymine (T) peptide nucleic acid (PNA) monomer is reported. Ferrocene carboxylic acid and (η-ethene) bis(triphenylphosphine)platinum(0) were su

Efficient route to C2 symmetric heterocyclic backbone modified cyclic peptides

(Chemical Equation Presented) A tandem dimerization-macrocyclization approach using 1,3-dipolar azide-alkyne cycloaddition reactions has been employed in the facile and convergent solution phase syntheses of C2 symmetric cyclic peptide scaffold