119274-75-8

Upstream product

• 1149-26-4 (S)-N-(benzyloxycarbonyl)valine 
• 109-76-2 Trimethylenediamine 
• 3496-11-5 2,5-dioxopyrrolidin-1-yl (2S)-2-(((benzyloxy)carbonyl)amino)-3-methylbutanoate 
• 119153-86-5 C₁₆H₂₁NO₆ 

Downstream Products

• 83852-29-3 (S,S)-N,N'-bis(phenylalanyl)-1,3-diaminopropane 

Relevant academic research and scientific papers

Molecular hydrogels from bolaform amino acid derivatives: A structure-properties study based on the thermodynamics of gel solubilization

Insight is provided into the aggregation thermodynamics associated to hydrogel formation by molecular gelators derived from L-valine and L-isoleucine. Solubility data from NMR measurements are used to extract thermodynamic parameters for the aggregation i

Cu2+ recognition by N,N′-benzylated bis(amino amides)

Two new C2-symmetric N,N′-benzylated bis(amino amides) have been synthesised and their interaction with different transition metals studied using a variety of techniques including UV-Vis and CD spectroscopy or ESI-MS. The determination of the c

Diamine acylation with amino acid derivatives: An example of proximity effect in organic reactivity induced by supramolecular aggregation

Unexpected high yields of diamide 3 are obtained in the reaction of 1,3-propanediamine with an activated ester of l-valine (1) under adverse proportions of the reactants, namely in the presence of an excess of 1,3-propanediamine. It is observed using different conditions that the yield of difunctionalized compound is considerably higher than that expected from a statistical distribution of products. Proximity effects associated to supramolecular interactions explain the described reactivity.

Di-Amido Gellant For Use In Consumer Product Compositions

The invention is to di-amido gellant that are suitable for use in consumer product compositions.

Coordination of Cu2+ Ions to C 2 Symmetric pseudopeptides derived from valine

The acid-base and coordination properties of a family of pseudopeptidic ligands with C2 symmetry derived from valine (4a-e) have been studied using a variety of techniques as a model for metal coordination in peptides and proteins. The Cu2+ cation has been selected for coordination studies, although, for comparison, some results for Zn2+ are also presented. Good agreement has been obtained between the results obtained by potentiometric titrations, spectroscopic analysis, and mass spectrometry (ESI) studies. These results highlight the potential for the use of ESI MS for characterizing the nature of the complex species formed. Clearly, the Cu 2+ complexes are much more stable than the Zn2+ complexes. While the role of the aliphatic spacer seems to be very minor in the case of the Zn2+ complexes, revealing the ability of this cation to accommodate different coordination environments, this role is critical in the case of Cu2+. Different complexes with 1:1 or 2:2 Cu2+:L stoichiometries can be formed according to the length of the spacer and the basicity of the media. This is fully illustrated by the resolution of the X-ray structures of two different Cu2+ complexes corresponding to the ligands containing a spacer with two methylene groups (ligand 4a, complex 6a [Cu2(H-1L)2](ClO4)2 with a 2:2 stoichiometry) and a propylene spacer (4b, complex 5b [CuH-2L] CH3CH2OH with a 1:1 stoichiometry).

Synthesis and evaluation of pseudopeptidic fluorescence pH probes for acidic cellular organelles: In vivo monitoring of bacterial phagocytosis by multiparametric flow cytometry

A new family of fluorescent anthracenic pH probes has been synthesized, chemically characterized, and their photophysical properties have been investigated by steady-state and time-resolved fluorescence spectroscopy. The ability of these compounds to monitor pH has been investigated in solution and it was found that molecules 1-12 can act as fluorescent sensors for pH in a range between 4.6 and 6.5. This range corresponds to the pH of acidic organelles in the cell (pH 4.5-6.0) for which a limited number of probes are described. The acid-base behavior of each sensor varies slightly depending on the nature of substituents close to the amines present in the molecules. Thus, the pK a of this family of compounds can be finely tuned by the appropriate selection of the synthetic building blocks at the design stage. To test the potential diagnostic applications of this family of probes, macrocyclic pseudopeptide 2 was used to monitor the phagocytosis of a culture of GFP-labelled bacteria by human monocytic cells U937 using flow cytometry as the analytical tool. It was found that the occurrence of bacterial killing was concomitant with the production of reactive oxygen species and a drop in pH, the latter monitored indirectly by macrocyclic sensor 2, which suggests its potential use for diagnostic purposes. A new family of anthracenic macrocycles has been synthesized that can act as fluorescent probes for pH in the range 4.6-6.5. The pKa values of these compounds can be finely tuned. In flow cytometry experiments, it was found that bacterial killing by human monocytes (U937) occurred with a simultaneous drop in pH, which was monitored by one of the macrocyclic sensors.

New chiral tetraaza ligands for the efficient enantioselective addition of dialkylzinc to aromatic aldehydes

A series of chiral tetraaza ligands were studied for the enantioselective addition of dialkylzinc to aldehydes. These bis(amino amide) ligands show high enantioselectivity in the addition of organozincs to aromatic aldehydes. Different structural elements on the ligands seem to play an important role in determining the observed enantioselectivity. Ligand 4b (N,N′-bis(N-l-valinyl)-1,3-diaminopropane, with an aliphatic spacer with 3C atoms) catalyzed the addition of Et2Zn to benzaldehyde, 1-naphtaldehyde, 4-methoxybenzaldehyde, and 4-chlorobenzaldehyde to give the corresponding alcohol products with excellent conversions and selectivities and with enantioselectivities of 99, 97, 98, and 82%, respectively. DFT calculations provide an understanding of the mechanism of the enantioselection process.

Synthetic macrocyclic peptidomimetics as tunable pH probes for the fluorescence imaging of acidic organelles in live cells

(Chemical Equation Presented) Acid test: Macrocyclic compounds that comprise a 9,10-anthracene subunit linked by a C2-symmetric peptidomimetic chain (see formula) are useful as fluorescent probes in a pH range of biomedical interest. Changes in

Self-assembly of small peptidomimetic cyclophanes

The self-assembly of a series of small peptidomimetic cyclophanes in organic solvents was studied. X-ray diffraction, NMR spectroscopy, and molecular modelling were used to understand the structural features of these self-assembling compounds both at the molecular and supramolecular level. The factors that could influence the formation of gels rather than crystals were studied and a model for the arrangement of molecules in the gel was proposed. Furthermore, scanning electron microscopy revealed that in some cases these compounds undergo a transcription of chirality when going from organogelator to helicoidal gel fibres.

Efficient macrocyclization of U-turn preorganized peptidomimetics: The role of intramolecular H-bond and solvophobic effects

Simple peptidomimetic molecules derived from amino acids were reacted with meta- and parabis(bromomethyl) benzene in acetonitrile to very efficiently yield macrocyclic structures. The cyclization reaction does not require high dilution techniques and seems to be insensitive to the size of the formed macrocycle. The analysis of data obtained by 1H NMR, single-crystal X-ray diffraction, fluorescence measurements, and molecular mechanics indicate that folded conformations can preorganize the system for an efficient cyclization. The role played by intramolecular hydrogen-bonding and solvophobic effects in the presence of folded conformations is analyzed.