21887-86-5

Upstream product

• 589-57-1 diethyl phosphorylchloridite 
• 1161-13-3 N-Cbz-L-Phe 
• 37440-07-6 methyl (R)-2-(benzyloxycarbonylamino)-3-phenylpropanoate 
• 501-53-1 benzyl chloroformate 
• 21685-51-8 D-phenylalanine methyl ester 
• 769922-77-2 (S)-benzyl (1-(1H-benzo[d][1,2,3]triazol-1-yl)-1-oxo-3-phenylpropan-2-yl)carbamate 
• 35909-92-3 N-carbobenzoxy-L-phenylalanine methyl ester 
• 7803-57-8 hydrazine hydrate 
• 63-91-2 L-phenylalanine 
• 28709-70-8 N-benzyloxycarbonyl-L-phenylalanine ethyl ester 
• 827624-64-6 Cbz(L)-phenylalanine-phthalimide 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 109453-49-8 (C₈H₇O₂)(NHCHCOO)(CH₂C₆H₅)(CO₂C₂H₅) 
• 3397-32-8 N-(benzyloxycarbonyl)-phenylalanine-N-hydroxysuccinimide ester 

Downstream Products

• 5276-63-1 N-(N-benzyloxycarbonyl-phenylalanyl)-phenylalanine ethyl ester; optically inactive substance 
• 74973-88-9 N-benzyloxycarbonyl-phenylalanyl=>phenylalanyl=>phenylalanine ethyl ester 
• 99215-68-6 Z-Phe-D-Pro-OEt 
• 142182-07-8 1-(N-carbobenzyloxy-L-phenylalanyl)-2-bromoacetyl hydrazine 
• 62023-57-8 (S)-1-(2'-benzyloxycarbonylamino-3'-phenylpropanoyl)-3,5-dimethylpyrazole 
• 1356072-73-5 benzyl (1S)-1-benzyl-2-{(2E/Z)-2-[(5-nitro-2-furyl)-methylene]hydrazine}-2-oxoethylcarbamate 
• 1356072-75-7 benzyl (1S)-1-benzyl-2-{(2E/Z)-2-[(5-nitro-2-thienyl)-methylene]hydrazine}-2-oxoethylcarbamate 
• 1429433-58-8 Cbz-Phe-AzaGly-Leu-OMe 
• 62067-14-5 (S)-benzyl 1-azido-1-oxo-3-phenylpropan-2-ylcarbamate 
• 1352815-91-8 C₂₉H₂₃N₃O₅ 
• 93788-26-2 (S,S)-bis(N-benzyloxycarbonylphenylalanyl)diaza-18-crown-6 
• 93767-77-2 (S,S)-bis(phenylalanyl)-18-crown-6 

Relevant academic research and scientific papers

Organogels formed in various organic solvents by different alkyl L-phenylalanine dihydrazide derivatives

A new group of organogelators, L-phenylalanine dihydrazide derivatives were synthesized, which can self-assemble in various organic solvents and turned them into thermally reversible physical supramolecular organogels at extremely low concentrations (2 w

An efficient, stereocontrolled and versatile synthetic route to bicyclic partially saturated privileged scaffolds

Herein, we describe the development of a simple, high yielding and stereocontrolled strategy for the synthesis of a series of triazolopiperazines and other biologically relevant fused scaffolds from optically active amino acids. This route was applied to the synthesis of 22 scaffolds containing new, previously inaccessible vectors and used to access a novel analogue of ganaplacide.

Transformations of β-aryl-N-Cbz-α,β-didehydro-α-amino esters with hydrazine hydrate

Cyclizations of Cbz-protected α,β-didehydro-β-arylalanine esters 1 with excess hydrazine hydrate afforded mixtures of the expected 3-pyrazolidinones 2 and the unexpected 1-amino-5-benzylidenehydantoins 6 and N-Cbz-β-arylalanine hydrazides 7. Presumably, the pyrazolidinones 2 and hydantoins 6 are formed as primary products via competitive 1,2- and 1,4-addition of hydrazine hydrate followed by cyclization, whereas β-arylalanine hydrazides 7 are formed as secondary products via reductive cleavage of the C(5)-N(1) bond in pyrazolidinones 2. The overall selectivity depends on the reaction time and on the β-substituent in the starting dehydroalanine ester 1.

Benzotriazole-mediated synthesis of aza-peptides: En route to an aza-leuenkephalin analogue

Novel N-(N-Pg-azadipeptidoyl)benzotriazoles 20a-e couple efficiently with α-amino acids 21a-e, dipeptides 22a-c, aminoxyacetic acid 23a, depsidipeptide 23b, and α-hydroxy-β-phenylpropionic acid 27 yielding, respectively, azatripeptides 24a-g, azatetrapeptides 25a,b, a hybrid azatripeptide with an oxyamide bond 26a, a hybrid azatetrapeptide with an ester bond 26b, and a hybrid azatripeptide with an ester bond 28. A new protocol for the synthesis of N-Pg-azatripeptides 33a,b and 35a,b, each containing a natural amino acid at the N-terminus, avoids the low coupling rates of the aza-amino acid residue and enables the solution-phase synthesis of an azaphenylalanine analogue of Leu-enkephalin 40.

Synthesis and Antitubercular Activity of Novel Amino Acid Derivatives

In this work, 17 new N-acylhydrazone derivatives of amino acids have been evaluated for their in vitro antibacterial activity against Mycobacterium tuberculosis H37Rv. The compounds 8b, 8e, 8f, 9a-d, and 10c exhibited an important minimum inhibitory concentration activity between 12.5 and 50μg/mL, which can be compared with that of the tuberculostatic drug d-cycloserine (20μg/mL). In this work 17 new N-acylhydrazone derivatives of amino acids have been evaluated for their in vitro antibacterial activity against Mycobacterium tuberculosis H37Rv. Eight compounds were non-cytotoxic and exhibited an important MIC activity between 12.5 and 50μg/mL, which can be compared with that of the tuberculostatic drug d-cycloserine (20μg/mL).

A favorable, narrow, δh Hansen-parameter domain for gelation of low-molecular-weight amino acid derivatives

In recent years, the design of new low-molecular-weight gelators (LMWGs) has attracted considerable attention because of the interesting supramolecular architectures as well as industrial applications. In this context, the role of the organic solvent in d

Combinatorial synthesis of 3,5-Dimethylene substituted 1,2,4-Triazoles

Combinatorial cyclizations of imidates and hydrazides with methylene linked R groups, generated from the corresponding nitriles and carboxylic acids, respectively, provided a large library of 3,5-dimethylene substituted 1,2,4- trizoles. 2011 Bentham Science Publishers Ltd.

Enantioselective synthesis of n-protected α-amino acid hydrazides

A new, mild, general, and efficient synthesis of N-protected α-amino acid hydrazides is described. This two-step preparation uses N-aminophthalimide as protected hydrazine to prepare N-protected α-amino acid hydrazide precursors, and subsequent dephthaloy

Azadipeptide nitriles: Highly potent and proteolytically stable inhibitors of papain-like cysteine proteases

(Chemical Presented) Nitrogen instead of carbon: Azadipeptide nitriles resulting from CH/N exchange in the P1 position (see picture) are hitherto unknown. To access these compounds by conversion of amino acid-derived hydrazides with cyanogen bromide both nitrogen atoms of the hydrazide must be substituted. Despite a methylated P2-P1 peptide bond, the azadipeptide nitriles show a strong inhibitory activity against cysteine proteases, and a high stability towards chymotryptic hydrolysis.

Modified amino acids

The present invention provides a compound of the general formula 1, wherein X is the connection between the CO-hydrazine and the NR1-oxalic acid or ester group, and uses and synthesis methods. These compounds represent amino acid derivatives, wherein the amine group is turned into an acidic group by the oxalic acid group and the carboxylic acid is turned into an amine functionality by the hydrazine group; as well as peptidomimetics comprising the compound and methods for their synthesis.