4892-10-8

Usage

InChI:InChI=1/C27H28N2O5/c1-33-26(31)24(18-21-13-7-3-8-14-21)28-25(30)23(17-20-11-5-2-6-12-20)29-27(32)34-19-22-15-9-4-10-16-22/h2-16,23-24H,17-19H2,1H3,(H,28,30)(H,29,32)/t23-,24-/m0/s1

Upstream product

• 1161-13-3 N-Cbz-L-Phe 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 96452-48-1 benzyl pyridin-2-yl carbonate 
• 501-53-1 benzyl chloroformate 
• 96452-61-8 N-(Benzyloxycarbonyl)-L-phenylalanin-2-pyridylester 
• 3397-32-8 N-(benzyloxycarbonyl)-phenylalanine-N-hydroxysuccinimide ester 
• 1059596-58-5 N-Cbz-L-phenylalanine p-tolylthiol ester 
• 101-83-7 N-cyclohexyl-cyclohexanamine 
• 63-91-2 L-phenylalanine 
• 26055-07-2 Z-Phe-OBT 
• 87072-42-2 Z-L-phenylalanine DCHA salt 
• 2578-84-9 N-benzyloxycarbonyl-L-phenylalanine p-nitrophenyl ester 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 117999-37-8 Z-ΔPhe-(S)-Phe-OMe 

Downstream Products

• 99260-33-0 H-Phe-Phe-OMe*HOAc 
• 183609-76-9 methyl (R)-1-{(S)-2-[(S)-2-amino-3-phenylpropanamido]-3-phenylpropanoyl}pyrrolidine-2-carboxylate 

Relevant academic research and scientific papers

An efficient amide-forming reaction using tributyltrichloromethylphosphonium chloride

An efficient and expeditious amide-forming reaction is described via a combination of tributylphosphine and carbon tetrachloride (in situ generation of tributyltrichloromethylphosphonium chloride) in the absence of tertiary amines.

4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium Toluene-4-sulfonate (DMT/NMM/TsO?) Universal Coupling Reagent for Synthesis in Solution

4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium toluene-4-sulfonate (DMT/NMM/TsO?), a representative member of the inexpensive and environmentally-friendly N-triazinylammonium family of sulfonates, has been found to be a very effective coupling reagent for the synthesis of amides, esters and peptides in solution. This study confirms the usefulness of DMT/NMM/TsO? for peptide synthesis in solution, starting from Z-, Fmoc-, and Boc-protected substrates as well as unnatural building blocks. Peptide synthesis with DMT/NMM/TsO? produced high yields, with high crude product purity and low risk of racemization. In all cases, stoichiometric amounts of reagents were used and the standard synthetic procedure, without the need for time-consuming optimization stages or expensive chromatographic purification. DMT/NMM/TsO? was also found to be very useful for the synthesis of oligopeptides using a fragment coupling strategy.

Mechanochemical Synthesis of Dipeptides Using Mg-Al Hydrotalcite as Activating Agent under Solvent-Free Reaction Conditions

Given the high demand for green and sustainable synthetic methods for the formation of amides and peptidic bonds, herein we report the efficient, solvent-free mechanochemical synthesis of dipeptides from N-protected amino acids and amino acid methyl ester

Design and synthesis of novel hydroxypyridinone derivatives as potential tyrosinase inhibitors

Two groups of novel hydroxypyridinone derivatives 6(a-e) and 12(a-c), were designed as potential tyrosinase inhibitors, and synthesized using kojic acid as a starting material. The tyrosinase inhibitory activity of these two groups was demonstrated to be potent, especially compounds 6e and 12a, whose IC50 values for monophenolase activity were 1.95 μM and 2.79 μM, respectively. Both of these values are lower than that of kojic acid (IC50 = 12.50 μM). Compounds 6e and 12a were investigated for the inhibitory effect on diphenolase activity. The results showed that the inhibitory mechanism of these two compounds was reversible and that the inhibitory type was a competitive-uncompetitive mixed-type. The values of IC50 of 6e and 12a on the diphenolase activity of tyrosinase were determined to be 8.97 μM and 26.20 μM, respectively. The inhibitory constants (KI and KIS) of 6e were determined as 17.17 μM and 22.09 μM, respectively; and the KI and KIS values of 12a were 34.41 μM and 79.02 μM, respectively. Compound 6e showed a greater ability to reduce copper and a stronger copper chelating ability than kojic acid.

Synthesis, bioactivity, docking and molecular dynamics studies of furan-based peptides as 20s proteasome inhibitors

Proteasome inhibitors are promising compounds for a number of therapies, including cardiovascular and eye diseases, diabetes, and cancers. We previously reported a series of furanbased peptidic inhibitors with moderate potencies against the proteasome b5 subunit, hypothesizing that the C-terminal furyl ketone motif could form a covalent bond with the catalytic residue, threonine 1. In this context, we describe further optimizations of the furan-based peptides, and a series of dipeptidic and tripeptidic inhibitors were designed and synthesized, aiming at improved potency and better solubility. Most of the tripeptidic inhibitors demonstrated improved potency and selectivity as b5 subunit inhibitors in both enzymatic and cellular assays, and good antineoplastic activities in various tumor cell lines were also observed. However, no inhibitory effects were observed for the dipeptidic compounds, which led us to presume that a noncovalent binding mode is adopted. Docking studies and molecular dynamics simulations were carried out to verify this presumption, with results showing that the distance between the furyl ketone motif and Thr1 is slightly too long to form covalent bond.

An efficient mechanochemical synthesis of amides and dipeptides using 2,4,6-trichloro-1,3,5-triazine and PPh3

A rapid, facile, and efficient mechanochemical synthesis of amides from carboxylic acids has been developed through an in situ acid activation with 2,4,6-trichloro-1,3,5-triazine and a catalytic amount of PPh3. Under room temperature solvent-drop grinding of the reactants in the presence of an inorganic base, a variety of carboxylic acids including aromatic acids, aliphatic acids, and N-protected α-amino acids undergo amidation to afford amides in moderate to excellent yields. The method is also compatible with Fmoc, Cbz, and Boc protecting groups which yields protected optically active dipeptides without detectable racemization.

A mild and efficient amide formation reaction mediated by P(OEt)3 and iodine

With the activation of P(OEt)3 and I2, carboxylic acids can smoothly react with various primary and secondary amines, affording a series of amides, including peptides without racemization. 31P NMR spectroscopy studies showed that carboxylic phosphoric mixed anhydride was the reactive intermediate and a possible mechanism was herein proposed.

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

Direct amidation of amino acid derivatives catalyzed by arylboronic acids: Applications in dipeptide synthesis

The direct amidation of amino acid derivatives catalyzed by arylboronic acids has been examined. The reaction was generally slow relative to simple amine-carboxylic acid combinations though proceeded at 65-68 °C generally avoiding racemization. 3,4,5-Trifluorophenylboronic and o-nitrophenylboronic acids were found to be the best catalysts, though for slower dipeptide formations, high catalyst loadings were required and an interesting synergistic catalytic effect between two arylboronic acids was discovered. Arylboronic acids can be used to catalyze the direct amide formation of protected amino acid derivatives. For less reactive amino acids, cooperative catalysis can be used involving two arylboronic acids, one electron-rich and one electron-deficient, at high catalyst loadings to give good conversions at moderate temperatures. Copyright

N-Triazinylammonium salts, a method of preparation and uses thereof

The invention provides inner quaternary N-triazinyl- ammonium salts of sulphonic acids, of the Formula 1, a method of preparation thereof and a use thereof as condensation reagents in condensation reactions.