3850-45-1

Upstream product

• 4801-69-8 N-Benzyloxycarbonyl-L-phenylalanin- 
• 7517-19-3 methyl (L)-leucinate hydrochloride 
• 84759-67-1 CBZ-ΔPhe-L-Leu-OMe 
• 67-56-1 methanol 
• 69193-13-1 Cbz-L-Phe-L-Leu-NH₂ 
• 687-51-4 H-L-Leu-NH₂ 
• 5241-56-5 benzyl [(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]carbamate 
• 35909-92-3 N-carbobenzoxy-L-phenylalanine methyl ester 
• 1059596-58-5 N-Cbz-L-phenylalanine p-tolylthiol ester 
• 1161-13-3 N-Cbz-L-Phe 
• 29842-94-2 (S)-tert-butyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-phenylpropanamido)-4-methylpentanoate 
• 3588-57-6 Z-DL-Phe-OH 
• 4313-73-9 N-[N-[(phenylmethoxy)carbonyl]-L-phenylalanyl]-L-leucine 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 4313-73-9 N-[N-[(phenylmethoxy)carbonyl]-L-phenylalanyl]-L-leucine 
• 111633-84-2 (2S)-2--4-methylpentan-1-ol 
• 118474-25-2 (S)-Bz-Phe-(S)-LeuOMe 
• 66253-29-0 (2S)-2--4-methylpentan-1-al 
• 119140-57-7 (S)-2-[(S)-2-(2,3-Diamino-propionylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid methyl ester 
• 119140-58-8 (S)-2-{(S)-2-[(2-{[(S)-2-Benzyloxycarbonylamino-3-(4-benzyloxy-phenyl)-propionylamino]-methyl}-4,5-dihydro-3H-imidazole-4-carbonyl)-amino]-3-phenyl-propionylamino}-4-methyl-pentanoic acid methyl ester 
• 84759-71-7 1, D-Ala², Leu⁵-OMe>Enkephalin 
• 1261486-24-1 Cbz-Phe-Leu-Ala-O-t-Bu 
• 106556-07-4 Z-Phe-Leu-Ala-NH₂ 
• 145763-51-5 (S)-2-{(S)-2-[2-((R)-2-{2-Benzyloxycarbonylamino-3-[4-(toluene-4-sulfonyloxy)-phenyl]-propionylamino}-propionylamino)-acetylamino]-3-phenyl-propionylamino}-4-methyl-pentanoic acid methyl ester 
• 145763-41-3 N-benzyloxycarbonyl-O-tosyl-(Z)dehydrotyrosyl-(R)alanyl-glycyl-(S)phenylalanyl-(S)leucine methyl ester 
• 83544-70-1 L-tyrosyl-D-alanylglycyl-L-phenylalanyl-L-leucine 2-aminoethylamide 
• 83891-98-9 N-benzyloxycarbonyl-L-tyrosyl-D-alanylglycyl-L-phenylalanyl-L-leucine 2-aminoethylamide 

Relevant academic research and scientific papers

Solar and Visible Light Assisted Peptide Coupling

Amino acid and peptide couplings are widely used in fields related to pharma and materials. Still, current peptide synthesis continues to rely on the use of expensive, water sensitive, and waste-generating coupling reagents, which are often prepared in mu

Tripeptide analogues of MG132 as protease inhibitors

The 26S proteasome and calpain are linked to a number of important human diseases. Here, we report a series of analogues of the prototypical tripeptide aldehyde inhibitor MG132 that show a unique combination of high activity and selectivity for calpains over proteasome. Tripeptide aldehydes (1–3) with an aromatic P3 substituent show enhanced activity and selectivity against ovine calpain 2 relative to chymotrypsin-like activity of proteasome. Docking studies reveal the key contacts between inhibitors and calpain to confirm the importance of the S3 pocket with respect to selectivity between calpains 1 and 2 and the proteasome.

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.

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.

Phosphorus oxychloride as an efficient coupling reagent for the synthesis of esters, amides and peptides under mild conditions

A mild method is described for the conversion of carboxylic acids into esters, amides, as well as peptides without racemization through carboxyl activation by the reagent combination of POCl3 and DMAP. Long chain alcohols could be converted to the corresponding ester in good yields. 31P NMR spectrum was used to detect phosphorus-containing intermediates in ongoing reactions directly, and a possible mechanism has been proposed based on these results. The Royal Society of Chemistry 2013.

HMDO-promoted peptide and protein synthesis in ionic liquids

Hexamethyldisiloxane (HMDO) has been developed to efficiently promote the metal-free direct coupling of an amino function of one cysteine-free peptide or protein and a C-terminal thioester of the second peptide in ionic liquids. The amide-coupling reaction proceeds smoothly under mild conditions to afford the corresponding products in good to excellent yields (63-94%). Peptide couplings were also achieved using in-situ-generated thioesters by the thioesterification of oxo esters.

Recyclable hypervalent iodine(III) reagent iodosodilactone as an efficient coupling reagent for direct esterification, amidation, and peptide coupling

A hypervalent iodine(III) reagent plays a novel role as an efficient coupling reagent to promote the direct condensation between carboxylic acids and alcohols or amines to provide esters, macrocyclic lactones, amides, as well as peptides without racemization. The regeneration of iodosodilactone (1) can also be readily achieved. The intermediate acyloxyphosphonium ion C from the activation of a carboxylic acid is thought to be involved in the present esterification reaction.

Metal-free direct amidation of peptidyl thiol esters with α-amino acid esters

Metal-free direct amidation of peptidyl thiol esters with α-amino acid esters in the presence of bis(trimethylsilyl) acetamide (BSA) has been developed. This general method provides convenient access to N-protected peptides in good yields under mild condi

Fully enzymatic N→C-directed peptide synthesis using C-terminal peptide α-carboxamide to ester interconversion

Chemoenzymatic peptide synthesis is potentially the most cost-efficient technology for the synthesis of short and medium-sized peptides with some important advantages. For instance, stoichiometric amounts of expensive coupling reagents are not required and racemisation does not occur rendering purification easier compared to chemical peptide synthesis. In this paper, a novel interconversion reaction of peptide C-terminal α-carboxamides into primary alkyl esters with alcalase was used to develop a fully enzymatic peptide synthesis strategy. For each elongation step a cost-efficient amino acid carboxamide building block was used followed by the interconversion of the elongated peptide carboxamide to the corresponding primary alkyl ester. These peptide esters are the starting materials for the next enzymatic peptide elongation step. Copyright