95852-71-4

Usage

Uses

Used in Pharmaceutical Research:
L-Leucinamide, L-tyrosyl-2-methylalanyl-2-methylalanyl-L-phenylalanylis used as a research compound for its potential role in drug development, given its unique peptide structure and the possibility of it exhibiting novel biological activities.
Used in Biochemical Studies:
In the field of biochemistry, L-Leucinamide, L-tyrosyl-2-methylalanyl-2-methylalanyl-L-phenylalanylis utilized as a model compound to study the interactions of its constituent amino acids and to understand the effects of such complex peptide structures on biological systems.
Used in Drug Development:
L-Leucinamide, L-tyrosyl-2-methylalanyl-2-methylalanyl-L-phenylalanylis used as a lead compound in the development of new pharmaceuticals, potentially targeting various diseases and conditions, given its complex nature and the therapeutic potential of its constituent amino acids.
Used in Medical Research:
In the medical research industry, L-Leucinamide, L-tyrosyl-2-methylalanyl-2-methylalanyl-L-phenylalanylis employed to investigate its biological properties, which may include effects on cell signaling, protein interactions, and other physiological processes relevant to human health and disease.

Upstream product

• 112883-29-1 N-Fmoc-Tyr-OH 
• 35661-40-6 N-Fmoc L-Phe 
• 94744-50-0 N-[(9H-fluoren-9-ylmethoxy)carbonyl]-α-aminoisobutyric acid 
• 139551-97-6 (S)-(9H-fluoren-9-yl)methyl (1-Amino-4-methyl-1-oxo-pentan-2-yl)carbamate 
• 110-89-4 piperidine 
• 35661-60-0 Fmoc-Leu-OH 
• 95852-51-0 Aib-Phe-Leu-NH₂ 
• 33019-85-1 Boc-Tyr-OH 
• 32909-56-1 Nα-pivaloyl-L-phenylalanine 
• 38678-59-0 L-Phe-L-Leu-NH₂ 
• 2666-93-5 (S)-Leu-OMe 
• 71989-38-3 Fmoc-Tyr(tBu)-OH 

Relevant academic research and scientific papers

Green solid-phase peptide synthesis 4. γ-Valerolactone and N-formylmorpholine as green solvents for solid phase peptide synthesis

Herein, we report the use of γ-valerolactone (GVL) and N-formylmorpholine (NFM) as DMF substitutes in polystyrene based SPPS. The solubility of selected amino acids and coupling reagents were studied in GVL and NFM, followed by their use in the successful synthesis of Aib-enkephalin pentapeptide (H-Tyr-Aib-Aib-Phe-Leu-NH2) and Aib-ACP decapeptide (H-Val-Gln-Aib-Aib-Ile-Asp-Tyr-Ile-Asn-Gly-NH2).

Microwave irradiation and COMU: a potent combination for solid-phase peptide synthesis

Here we demonstrate the compatibility of Oxyma-based uronium-type coupling reagent COMU with microwave-assisted peptide synthesizers. Consistent with previous reports, COMU displayed higher efficiency than benzotriazole classical immonium salts HATU and H

Boosting Fmoc Solid-Phase Peptide Synthesis by Ultrasonication

We investigated the ultrasonication-mediated effects on the Fmoc-based solid-phase peptide synthesis (SPPS). Our study culminated with the development of an ultrasound-assisted strategy (US-SPPS) that allowed for the synthesis of different biologically active peptides (up to 44-mer), with a remarkable savings of material and reaction time. Noteworthy, ultrasonic irradiation did not exacerbate the main side reactions and improved the synthesis of peptides endowed with "difficult sequences", placing the US-SPPS among the current high-efficient peptide synthetic strategies.

Oxyma-T, expanding the arsenal of coupling reagents

Herein, we report a new oxime-based additive (Oxyma-T) with a similar structure to HONM and Oxyma-B for use in peptide synthesis. Oxyma-T produces less racemization than HOBt, HOAt, OxymaPure, and Oxyma-B during the stepwise solution-phase synthesis of Z-Phg-Pro-NH2. Moreover, it exhibits superior coupling efficiency in comparison to HOBt during the SPPS of an Aib-enkephalin pentapeptide. Racemization during segment coupling follows the order: HOBt?>?Oxyma-T?>?OxymaPure?>?HOAt?>?Oxyma-B.

Peptide synthesis beyond DMF: THF and ACN as excellent and friendlier alternatives

To date, DMF has been considered as the only solvent suitable for peptide synthesis. Here we demonstrate the capacity of THF and ACN, which are friendlier solvents than DMF, to yield the product in higher purity than DMF. Using various peptide models, both THF and ACN reduced racemization in solution-phase and solid-phase synthesis when compared with DMF. Moreover, the use of ACN and THF in the solid-phase peptide synthesis of hindered peptides, such as Aib-enkephalin pentapeptide and Aib-ACP decapeptide, in combination with a complete polyethylene glycol resin (ChemMatrix), gave a better coupling efficiency than DMF. This journal is

EDC·HCl and potassium salts of oxyma and oxyma-b as superior coupling cocktails for peptide synthesis

Nowadays, DIC is the most widely used carbodiimide for solid-phase peptide synthesis, while EDC·HCl is mostly used only for solution-phase synthesis. In this paper, we report new coupling cocktails containing EDC·HCl in combination with potassium salts of OxymaPure and Oxyma-B (i.e., K-Oxyma and K-Oxyma-B, respectively). These reagent cocktails gave spectacular purity compared to DIC/classical N-hydroxylamine derivatives in the solid-phase peptide synthesis of the Aib-enkephaline (Aib = 2-aminoisobutyric acid) pentapeptide (H-Tyr-Aib-Aib-Phe-Leu-NH2), a hindered peptide. Furthermore, we found that the EDC·HCl/K-Oxyma combination can be used with DMF, THF, or MeCN as the solvent. The optimized cocktail gave less racemization than benzotriazole derivatives, but slightly more than OxymaPure and Oxyma-B during stepwise solution-phase peptide synthesis. We have shown that combinations of rather simple and green reagents, such as EDC·HCl and the potassium salt of OxymaPure or Oxyma-B, give unique results in terms of yield and low levels of racemization. We envisage a broad application of these reagents in solid-phase and solution synthesis, and especially in the preparation of peptide-based nanomaterials.

4-(4,6-Di[2,2,2-trifluoroethoxy]-1,3,5-triazin-2-yl)-4-methylomorpholinium tetrafluoroborate. Triazine-based coupling reagents designed for coupling sterically hindered substrates

4-(4,6-Di[2,2,2-trifluoroethoxy]-1,3,5-triazin-2-yl)-4-methylomorpholinium tetrafluoroborate (DFET/NMM/BF4) was prepared and used as a reagent for coupling sterically hindered substrates. The formation of the appropriate triazine "superactive" ester in a reaction of DFET/NMM/BF4 with carboxylic acids was confirmed. The efficiency of the reagent has been studied in the synthesis of Leu-enkephaline pentapeptide carried out on a Fmoc-RinkAmide-AM-PS resin, by systematically modifying the -Gly-Gly- fragment for N-methyl or α,α-disubstituted residues and compared with the efficiency of classic aminium salt 2-(1H-benzotriazole-1-yl)-1,1,3,3- tetramethyluronium tetrafluoroborate (TBTU) under a variety of reaction conditions. In syntheses of Aib-Aib (Aib: α-aminoisobutyric acid), MeVal-MeVal, and MeLeu-MeLeu, the considerably superior performance of enkephaline analogues was obtained for DFET/NMM/BF4 relative to TBTU, regardless of reaction conditions. Analysis of the couplings involving triazine reagent suggests that factors controlling efficiency of coupling sterically hindered substrates are the structure of the leaving group permitting formation of the cyclic intermediate or cyclic transition state and the absence of strongly solvating solvents. It has to be considered as highly probable that the absence of strongly solvating milieu favors cyclic intermediates or the cyclic transition state. Arrangement of both components into the cyclic intermediate or cyclic transition state by accumulation of the geminal (vicinal) substituents effect (known as the Thorpe-Ingold effect) would compensate retardation of the coupling process caused by steric hindrance.

Ethyl 2-Cyano-2-(hydroxyimino)acetate (Oxyma): An efficient and convenient additive used with tetramethylfluoroformamidinium hexafluorophosphate (TFFH) to replace 1-hydroxybenzotriazole (HOBt) and 1-hydroxy-7-azabenzotriazole (HOAt) during peptide synthesis

The appropriateness of ethyl 2-cyano-2-(hydroxyimino)acetate (Oxyma) as a substitute for benzotriazole-based additives, for use in the TFFH approach for peptide synthesis, is discussed in terms of its capacity to control racemization, its coupling efficiency in difficult couplings either for stepwise or segment coupling in solution- and solid-phase coupling. In addition, Boc-based solution-phase peptide synthesis and its stability in the presence of growing peptide chains were studied. Oxyma displayed remarkable results in terms of racemization depression together with impressive coupling efficiency in both solution- and solid-phase synthesis. Furthermore, Oxyma suggests a lower risk of explosion than HOBt and HOAt.

COMU: A safer and more effective replacement for benzotriazole-based uronium coupling reagents

We describe a new family of uronium-type coupling reagents that differ in their iminium moieties and leaving groups. The presence of the morpholino group in conjunction with an oxime derivative-especially ethyl 2-cy ano-2- (hydroxyimino) acet ate (Oxyma)-had a marked influence on the solubilities, stabilities, and reactivities of the reagents. Finally, the new uronium salt derived from Oxyma (COMU) performed extremely well in the presence of only 1 equiv of base, thereby confirming the effect of the hydrogen bond acceptor in the reaction. COMU also showed a less hazardous safety profile than the benzotriazolebased HDMA and HDMB, which exhibited unpredictable autocatalytic decompositions. Furthermore, the Oxyma moiety contained in COMU suggests a lower risk of explosion than in the case of the benzotriazole derivatives.

Oxyma: An efficient additive for peptide synthesis to replace the benzotriazole-based HOBt and HOAt with a lower risk of explosion

Oxyma [ethyl 2-cyano-2-(hydroxyimino)acetate] has been tested as an additive for use in the carbodiimide approach for formation of peptide bonds. Its performance in relation to those of HOBt and HOAt, which have recently been reported to exhibit explosive properties, is reported. Oxyma displayed a remarkable capacity to inhibit racemization, together with im-pressive coupling efficiency in both automated and manual synthesis, superior to those of HOBt and at least comparable to those of HOAt, and surpassing the latter coupling agent in the more demanding peptide models. Stability assays showed that there was no risk of capping the resin under standard coupling conditions. Finally, calorimetry assays (DSC and ARC) showed decomposition profiles for benzotriazolebased additives that were consistent with their reported explosivities and suggested a lower risk of explosion in the case of Oxyma.