35373-94-5

Upstream product

• 214475-40-8 ZPheNHPr 
• 3397-32-8 N-(benzyloxycarbonyl)-phenylalanine-N-hydroxysuccinimide ester 
• 107-10-8 propylamine 
• 63-91-2 L-phenylalanine 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 1161-13-3 N-Cbz-L-Phe 
• 3081-24-1 H-Phe-OEt 

Downstream Products

• 1116686-72-6 (S)-3-phenyl-N₁-phenylpropane-1,2-diamine 
• 1594770-03-2 C₄₅H₅₉N₅O₁₀ 
• 1594769-62-6 ZAspPheAspPheNHPr 
• 1594769-92-2 C₂₁H₂₇N₃O₂ 
• 1594770-07-6 C₄₅H₅₉N₅O₁₀ 
• 1594769-66-0 C₃₇H₄₃N₅O₁₀ 
• 1594770-08-7 C₄₅H₅₉N₅O₁₀ 
• 1594769-67-1 ZPheAspAspPheNHPr 
• 1594769-84-2 C₂₉H₃₃N₃O₄ 
• 1594769-91-1 C₂₈H₃₇N₃O₆ 
• 1594769-99-9 C₂₀H₃₁N₃O₄ 

Relevant academic research and scientific papers

Protecting-Group-Free Amidation of Amino Acids using Lewis Acid Catalysts

Amidation of unprotected amino acids has been investigated using a variety of ‘classical“ coupling reagents, stoichiometric or catalytic group(IV) metal salts, and boron Lewis acids. The scope of the reaction was explored through the attempted synthesis of amides derived from twenty natural, and several unnatural, amino acids, as well as a wide selection of primary and secondary amines. The study also examines the synthesis of medicinally relevant compounds, and the scalability of this direct amidation approach. Finally, we provide insight into the chemoselectivity observed in these reactions.

Direct amidation of unprotected amino acids using B(OCH2CF3)3

A commercially available borate ester, B(OCH2CF3)3, can be used to achieve protecting-group free direct amidation of α-amino acids with a range of amines in cyclopentyl methyl ether. The method can be applied to the synthesis of medicinally relevant compounds, and can be scaled up to obtain gram quantities of products.

Structural insight into the aggregation of l-prolyl dipeptides and its effect on organocatalytic performance

NMR and organocatalytic studies of four dipeptides derived from l-proline are described. Results indicate that important conformational changes around the catalytic l-proline moiety are observed for free dipeptides upon changing the adjacent amino acid. Also, an aggregation process is detected as the concentration increases. The self-association of the dipeptides has been fitted to a cooperative binding model. All the compounds have been assayed as catalysts for the conjugated addition of cyclohexanone to trans-β-nitrostyrene in toluene. In agreement with the structural studies, noticeable changes in the catalytic performance are detected upon changing the catalyst concentration, as the catalyst is activated by self-aggregation. This journal is

Tetrapeptidic molecular hydrogels: Self-assembly and Co-aggregation with amyloid fragment Aβ1-40

A new family of isomeric tetrapeptides containing aromatic and polar amino acid residues that are able to form molecular hydrogels following a smooth change in pH is described. The hydrogels have been studied by spectroscopic and microscopic techniques showing that the peptide primary sequence has an enormous influence on the self-assembly process. In particular, the formation of extended hydrophobic regions and the appearance of π-stacking interactions have been revealed as the driving forces for aggregation. Moreover, the interaction of these compounds with amyloid peptidic fragment Aβ1-40 has been studied and some of them have been shown to act as templates for the aggregation of this peptide into non-β-sheet fibrillar structures. These compounds could potentially be used for the capture of toxic, soluble amyloid oligomers. Copyright

Mechanistic insight into the lability of the benzyloxycarbonyl (Z) group in N-protected peptides under mild basic conditions

An unexpected lability of the benzyloxycarbonyl (Z) protecting group under mild basic conditions at room temperature is explained by a mechanism based on anchimeric assistance. It is found that the vicinal amide group stabilises the tetrahedral intermediate formed after nucleophilic addition of hydroxide to the carbonyl of the Z group. This effect operates in N-protected tripeptides and tetrapeptides but Z-protected dipeptides are stable under the same conditions due to blockage of the vicinal amide NH by intramolecular H-bonding with the terminal carboxylate moiety. Copyright

Organocatalyzed highly enantioselective michael additions of malonates to enones by using novel primary-secondary diamine catalysts

A novel primary-secondary diamine catalyst readily available from primary amino acids in three steps for the highly enantioselective Michael additions of malonates to α,β-unsaturated ketones was reported. The Michael reaction of dimethyl malonate with benzylideneacetone was selected as a model reaction for catalyst evaluation. The length of the alkyl chain is found to influence the catalytic abilities of the catalysts and the n-propylated catalyst gave the highest yield and ee value. The addition of a series of malonates to enone performed under the optimized conditions is found to be sensitive to the steric hinderance on the malonates. Heterocyclic furan enone is found to perform well to give the desired product in 92% yield and 99% ee, while no decrease in yield and ee value is observed for sterically hindered enone.

Synthesis of chiral tropopodands having l-amino acid moieties and ability of their metal complexes as an asymmetric catalyst

Optical active tropopodans (10 and 11) having neutral l-amino acids and l-histidine moieties were synthesized. Within their metal complexes, Pd complexes of histidine-tropopodands (11b and 11c) bearing bulky amide moieties showed good ability as an asymmetric catalyst in conjugate addition.

Nickel complexes from α-amino amides as efficient catalysts for the enantioselective Et2Zn addition to benzaldehyde

Ni2+ complexes derived from simple α-amino amides catalyze very efficiently the addition of Et2Zn to benzaldehyde, giving (S)-1-phenylethanol as the major isomer in most cases (94% yield, 97% ee for R=Bn). The nature of the substituent on the amide nitrogen atom seems to play a key role in determining the asymmetric induction observed.