878627-28-2

Upstream product

• 848352-99-8 5-(benzyloxycarbonyl)-1H-pyrrole-2-carboxylic acid 
• 219511-71-4 tert-butyl carbamimidoylcarbamate 

Downstream Products

• 878627-34-0 C₆₀H₈₄N₁₀O₁₅ 
• 878627-31-7 C₂₆H₃₄N₄O₇ 
• 878627-33-9 C₂₅H₃₂N₄O₇ 
• 950743-79-0 C₂₇H₃₆N₆O₈ 

Relevant academic research and scientific papers

Synthesis and self-association properties of flexible guanidiniocarbonylpyrrole-carboxylate zwitterions in DMSO: Intra- versus intermolecular ion pairing

(Chemical Equation Presented) We have synthesized a new class of flexible zwitterions 6a-e, in which a carboxylate is linked via an alkyl chain with variable length (one to five methylene groups) to a guanidiniocarbonylpyrrole cation. The self-association properties of these zwitterions were determined by NMR dilution studies in DMSO and by ESI-MS experiments. The stability and hence also the size of the aggregates formed via self-assembly is critically dependent on the length and therefore flexibility of the spacer. Whereas the smallest zwitterion 6a forms large aggregates already at low concentrations, the more flexible zwitterions only form small oligomers (6b) or dimers (6c-e) at much larger concentrations. The differences between the five zwitterions can be explained based on the different extent of intramolecular ion pairing within the monomers. Any intramolecular ion pairing, which becomes possible with increasing linker length, stabilizes the monomer and therefore destabilizes any oligomer.

A facile and efficient multi-gram synthesis of N-protected 5-(guanidinocarbonyl)-1H-pyrrole-2-carboxylic acids

The synthesis of two versatile building blocks for supramolecular anion binding motifs, 5-(N-Boc-guanidinocarbonyl)-1H-pyrrole-2-carboxylic acid (1) and 5-(N-Cbz-guanidinocarbonyl)-1H-pyrrole-2-carboxylic acid (2) is reported. Using these building blocks, a guanidiniocarbonyl-pyrrole anion binding site can easily be introduced into more complex molecules by using standard amide coupling conditions. Both syntheses can be performed on a multi-gram scale. The products are obtained in pure form and can be stored as solids without decomposition. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Oxoanion binding by flexible guanidiniocarbonyl pyrrole-ammonium bis-cations in water

(Chemical Equation Presented) The syntheses of several bis-cations 1-5 with a simple primary ammonium cation attached via flexible linkers of varying length to a guanidiniocarbonyl pyrrole oxo anion binding site are reported. In UV-binding studies in aqueous buffer solution these bis-cations showed efficient binding of various N-acetyl amino acid carboxylates. However, complex affinity is significantly depending on both the anion and the length of the linker in the bis-cation. With increasing linker length, complex stability first increases until an optimum is reached for bis-cation 3 with a C4-linker. Then the complex stability decreases again. The best binding substrate in this series is N-acetyl phenyl alanine, most likely due to additional cation-π-interactions between the aromatic ring and the guanidiniocarbonyl pyrrole cation. The formation of the complex between bis-cation 3 and N-acetyl phenyl alanine carboxylate was investigated further by fluorescence titrations and NOE studies, as well as molecular mechanics calculations.