100429-39-8

Upstream product

• 10065-72-2 L-Alanine methyl ester 
• 1161-13-3 N-Cbz-L-Phe 
• 4816-89-1 Cbz-Phe-OCH₂CONH₂ 
• 122751-39-7 Z-Phe-OPyCl 
• 2491-20-5 L-alanine methyl ester hydrochloride 
• 87072-42-2 Z-L-phenylalanine DCHA salt 
• 3588-57-6 Z-DL-Phe-OH 
• 63-91-2 L-phenylalanine 
• 67-56-1 methanol 
• 65118-54-9 N-(benzyloxycarbonyl)phenylalanyl-alanine amide 
• 35909-92-3 N-carbobenzoxy-L-phenylalanine methyl ester 
• 501-53-1 benzyl chloroformate 
• 14316-06-4 D-alanine methyl ester hydrochloride 
• 133010-22-7 benzyl (S)-(1-fluoro-1-oxo-3-phenylpropan-2-yl)carbamate 

Downstream Products

• 62076-46-4 Z-L-Phe-L-βClAla-OMe 
• 65118-54-9 N-(benzyloxycarbonyl)phenylalanyl-alanine amide 
• 3338-39-4 N-benzyloxycarbonyl-L-phenylalanyl-L-alanine 
• 115514-18-6 (S)-methyl 2-(5-((S)-1-(((benzyloxy)carbonyl)amino)-2-phenylethyl)-1H-tetrazol-1-yl)propanoate 
• 3235-53-8 Z-Phe-Ala-NHNH₂ 
• 80870-39-9 D-phenylalanine-L-alanine methylester 
• 223271-89-4 {(S)-1-[(S)-1-((S)-1-Carbamoyl-4-guanidino-butylcarbamoyl)-ethylcarbamoyl]-2-phenyl-ethyl}-carbamic acid benzyl ester 
• 143087-83-6 Z-L-Phe-L-Ala-L-Leu-NH₂ 
• 167498-27-3 AQ₅₇₃₁₈₈ 
• 1432584-89-8 (Z)-N-((S)-2-((S)-2-(((benzyloxy)carbonyl)amino)-3-phenylpropanamido)propylidene)-2-(((S)-1-(tert-butoxy)-3-methyl-1-oxobutan-2-yl)amino)-2-oxoethanamine oxide 
• 1432584-90-1 (5S,8S,14S)-tert-butyl 5-benzyl-14-isopropyl-8-methyl-3,6,9,12-tetraoxo-1-phenyl-2-oxa-4,7,10,13-tetraazapentadecan-15-oate 
• 106556-08-5 Z-L-Phe-L-Ala-OCam 
• 69193-13-1 Cbz-L-Phe-L-Leu-NH₂ 
• 167498-32-0 benzyl (S,S)-1-(1-hydroxypropan-2-ylamino)-1-oxo-3-phenylpropan-2-ylcarbamate 

Relevant academic research and scientific papers

Sulfonate esters of 1-hydroxypyridin-2(1H)-one and ethyl 2-cyano-2-(hydroxyimino)acetate (Oxyma) as effective peptide coupling reagents to replace 1-hydroxybenzotriazole and 1-hydroxy-7-azabenzotriazole

A new family of sulfonate ester-type coupling reagents is described which differs in its leaving group. The sulfonate ester coupling reagents ethyl 2-cyano-2-(naphthalen-2-ylsulfonyloxyimino)acetate (NpsOXY), and ethyl 2-cyano-2-(tosyloxyimino)acetate (Ts

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

Development of Triazinone-Based Condensing Reagents for Amide Formation

Novel triazinone-based condensing reagents have been developed. The palladium-catalyzed O-N allylic rearrangement of 2-(allyloxy)-4,6-dichloro-1,3,5-triazine and subsequent regioselective substitution using alcohols and an amine afforded chlorotriazinones, which can be readily converted using N-methylmorpholine into the corresponding condensing reagents. The condensation of carboxylic acids and amines using these reagents proceeded to afford the desired amides in good yields. In comparison with 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride, the newly synthesized triazinone-based condensing reagents exhibited higher reactivity.

A Bottom-Up Approach to Preserve Thioamide Residue Stereochemistry during Fmoc Solid-Phase Peptide Synthesis

Thioamides are useful biophysical probes for the study of peptide structure and folding. The α-C stereochemistry of thioamide amino acids, however, is easily epimerized during solid-phase peptide synthesis (SPPS), which limits the sequence space that is a

N-Hydroxyamide-containing Heterocycles. New Effective Additives for Peptide Synthesis by the Dicyclohexylcarbodiimide Method

N-Hydroxyamide-containing heterocycles, 1-hydroxy-4,6-dimethyl-2(1H)-pyrimidinone and -5,6-dimethyl-2(1H)-pyrazinone, are prepared.Judging from the result of model dipeptide (Z-Ala-Phe-OMe) formation, these compounds are found to be new effective additive

Development of a triazinedione-based dehydrative condensing reagent containing 4-(dimethylamino)pyridine as an acyl transfer catalyst

A new triazinedione-based reagent, (N,N′-dialkyl)triazinedione-4-(dimethylamino)pyridine (ATD-DMAP) was developed for the operationally simple dehydrative condensation of carboxylic acids. This reagent comprises an ATD core and DMAP as the leaving group, which is liberated into the reaction system to accelerate acyl transfer reactions. Upon adding ATD-DMAP to a mixture of carboxylic acids and alcohols in the presence of an amine base, the corresponding esters were formed rapidly at room temperature. Moreover, dehydrative condensation between carboxylic acids and amines using ATD-DMAP proceeded in high yield.

N-acyltriazinedione; a novel acylating reagent synthesized from a triazinone-type condensing reagent

In this paper, we report the synthesis of N-acyltriazinedione via the unexpected O–N acyl rearrangement of acyloxytriazinone and its utility as an acylating reagent. N-Acyltriazinedione can be isolated by silica gel column chromatography and reacts with amines in the absence of any base to give the corresponding amides in good yields.

Optimization and anti-cancer properties of fluoromethylketones as covalent inhibitors for ubiquitin C-terminal hydrolase L1

The deubiquitinating enzyme (DUB) UCHL1 is implicated in various disease states including neurodegenerative disease and cancer. However, there is a lack of quality probe molecules to gain a better understanding on UCHL1 biology. To this end a study was carried out to fully characterize and optimize the irreversible covalent UCHL1 inhibitor VAEFMK. Structure-activity relationship studies identified modifications to improve activity versus the target and a full cellular characterization was carried out for the first time with this scaffold. The studies produced a new inhibitor, 34, with an IC50 value of 7.7 μM against UCHL1 and no observable activity versus the closest related DUB UCHL3. The molecule was also capable of selectively inhibiting UCHL1 in cells and did not demonstrate any discernible off-target toxicity. Finally, the molecule was used for initial probe studies to assess the role of UCHL1 role in proliferation of myeloma cells and migration behavior in small cell lung cancer cells making 34 a new tool to be used in the biological evaluation of UCHL1.

Trimodular Solution-Phase Protocol for Rapid Large-Scale Synthesis of Hydrogen Bond Surrogate-Constrained α-Helicomimics

Scalability, optimal reagent usage, high yields, easy isolation, and cost-effectiveness, are key for the applicability of synthetic methodologies in the production of potential therapeutics. Hydrogen bond surrogate (HBS) constrained α-helical peptides (α-helicomimics) have shown promise as therapeutics based on their efficiency to interfere with protein-biomolecular interactions. The propyl HBS-constrained α-helicomimics have shown the highest helicities in both single turn and extended, α-helices (STαH, EαH). Here we present a solution-phase synthetic (SPS) method, for the rapid, large-scale, low-cost synthesis of libraries of STαH and EαH in high yields. The key to efficiency is our trimodular (M1, M2, M3) synthetic protocol where M1 is a library of HBS-linked peptidomimetic synthons of both STαH and EαH; M2 and M3 are desired oligopeptide libraries. Advantages of the trimodular method over conventional unimodular methods are demonstrated through the synthesis of large-scale libraries of M1, STαH, and EαH.

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.