126727-23-9

Upstream product

• 15761-38-3 L-N-Boc-Ala 
• 62-53-3 aniline 
• 109208-68-6 Boc-Ala-O-COO-isoBu 
• 24424-99-5 di-tert-butyl dicarbonate 
• 3392-05-0 Boc-Ala-O-N-hydroxysuccinimide 

Downstream Products

• 917610-55-0 (S)-2-(tert-butoxycarbonylamino)-1-(2'-aminophenyl)propan-1-one 
• 6304-98-9 (S)-N-benzoyl-alanine anilide 
• 69079-80-7 alanyl-alanine-anilide 

Relevant academic research and scientific papers

Design, synthesis, and insecticidal activities of novel diamide derivatives with alpha-amino acid subunits

A series of diamide derivatives containing α-amino acids were designed and synthesized. These compounds were evaluated for their insecticidal activities against Plutella xylostella, Mythimna separate, Myzus persicae, and Tetranychus cinnabarinus. Most of the title compounds containing an l-phenylglycine skeleton were endowed with good activities at the concentration of 500 mg·L?1. Compounds (R)-A6 showed a potential value for further optimization as an insecticidal lead with the LC50 value of 86.8 mg·L?1.

Clickable coupling of carboxylic acids and amines at room temperature mediated by SO2F2: A significant breakthrough for the construction of amides and peptide linkages

The construction of amide bonds and peptide linkages is one of the most fundamental transformations in all life processes and organic synthesis. The synthesis of structurally ubiquitous amide motifs is essential in the assembly of numerous important molecules such as peptides, proteins, alkaloids, pharmaceutical agents, polymers, ligands and agrochemicals. A method of SO2F2-mediated direct clickable coupling of carboxylic acids with amines was developed for the synthesis of a broad scope of amides in a simple, mild, highly efficient, robust and practical manner (>110 examples, >90% yields in most cases). The direct click reactions of acids and amines on a gram scale are also demonstrated using an extremely easy work-up and purification process of washing with 1 M aqueous HCl to provide the desired amides in greater than 99% purity and excellent yields.

Amine Activation: N-Arylamino Acid Amide Synthesis from Isothioureas and Amino Acids

N-arylamino acid amides have been synthesized via a novel method based on N-arylamine activation into isothioureas followed by reaction with amino acids under iron catalysis. The activated N-arylamines are easily prepared using a three-component reaction with commercial reagents, tert-butylisocyanide and S-phenyl benzenethiosulfonate. The protocol shows a broad functional group compatibility, with respect to side chain functionality of the amino acid (e. g. aliphatic and aromatic OH, (hetero)aromatic NH, amide NH, thioether), and the chiral amino acids do not undergo epimerization. The mechanism of the new amide synthesis has been studied. (Figure presented.).

A novel N-terminal degradation reaction of peptides via N-amidination

The cleavage of amide bonds requires considerable energy. It is difficult to cleave the amide bonds in peptides at room temperature, whereas ester bonds are cleaved easily. If peptide bonds can be selectively cleaved at room temperature, it will become a powerful tool for life science research, peptide prodrug, and tissue-targeting drug delivery systems. To cleave a specific amide bond at room temperature, the decomposition reaction of arginine methyl ester was investigated. Arginine methyl ester forms a dimer; the dimer releases a heterocyclic compound and ornithine methyl ester at room temperature. We designed and synthesized N-amidinopeptides based on the decomposition reaction of arginine methyl ester. Alanyl-alanine anilide was used as the model peptide and could be converted into N-degraded peptide, alanine anilide, via an N-amidination reaction at close to room temperature. Although the cleavage rate in pH 7.4 phosphate buffered saline (PBS) at 37?°C was slow (t1/2?=?35.7?h), a rapid cleavage rate was observed in 2% NaOH aq (t1/2?=?1.5?min). To evaluate the versatility of this reaction, a series of peptides with Lys, Glu, Ser, Cys, Tyr, Val, and Pro residue at the N-terminal were synthesized; they showed rapid cleavage rates of t1/2values from 1?min to 10?min.

DIPEPTIDOMIMETICS AS INHIBITORS OF HUMAN IMMUNOPROTEASOMES

The compounds of the present invention are represented by the following compounds having Formula (I), where the substituents R1, R4, L, M, X, Y, and s are as defined herein. The compounds of the present invention are also represented by the following compounds having Formula (Ia), Formula (lb), or Formula (Ic), where the substituents R1-R4, Rx, Ry, X, Y, and s are as defined herein. These compounds are used in the treatment of cancer, immunologic disorders, autoimmune disorders, neurodegenerative disorders, or inflammatory disorders or for providing immunosuppression for transplanted organs or tissues.

Hybrid Diphenylalkyne-Dipeptide Oligomers Induce Multistrand β-Sheet Formation

Functionalized diphenylalkynes provide a template for the presentation of protein-like surfaces composed of multistrand β-sheets. The conformational properties of three-, four-, and seven-stranded systems have been investigated in the solid- and solution-state. This class of molecule may be suitable for the mediation of therapeutically relevant protein-protein interactions. β-Sheets: Functionalized diphenylalkynes provide a template for the presentation of protein-like surfaces composed of multi-strand β-sheets. The conformational properties of three-, four-, and seven-stranded systems have been investigated in the solid- and solution-state. This class of molecule may be suitable for the mediation of therapeutically relevant protein-protein interactions.

Remarkable shape-sustaining, load-bearing, and self-healing properties displayed by a supramolecular gel derived from a bis-pyridyl-bis-amide of L -phenyl alanine

A series of bis-amides decorated with pyridyl and phenyl moieties derived from L-amino acids having an innocent side chain (L-alanine and L-phenyl alanine) were synthesized as potential low-molecular-weight gelators (LMWGs). Both protic and aprotic solven

Synthesis of highly substituted imidazolidine-2,4-dione (Hydantoin) through Tf2O-mediated dual activation of Boc-protected dipeptidyl compounds

Highly substituted chiral hydantoins were readily synthesized from simple dipeptides in a single step under mild conditions. This reaction proceeded through the dual activation of an amide and a tert-butyloxycarbonyl (Boc) protecting group by Tf2O-pyridine. This method was successfully applied in the preparation of a variety of biologically active compounds, including drug analogs and natural products.

Synthesis and anticonvulsant activity of some 2/3- benzoylaminopropionanilide derivatives

In this study, the synthesis and anticonvulsant properties of sixteen 2/3-benzoylaminopropionanilide derivatives were described. Molecular design of the compounds has been based on the modification of lacosamide which is a functionalized amino acid with a novel anticonvulsant activity. The structural confirmation of the title compounds was achieved by spectral and analytical data. The anticonvulsant activity profile of synthesized compounds was determined by maximal electroshock (MES) and subcutaneous metrazole (scMet) seizure tests, whereas their neurotoxicity was examined using rotarod test. All these tests were performed in accordance with the procedures of the Antiepileptic Drug Development (ADD) program. The majority of the compounds were effective in the MES or scMet screening tests. None of the compounds showed neurotoxicity according to the rotarod test at studied doses. Most active compounds in the series were 3, 12 and 13, which bearing 2-methyl, 2-ethyl and 2-isopropyl substituent on the N-phenyl ring, respectively. Georg Thieme Verlag KG Stuttgart - New York.

A three-component reaction based on a remote-group-directed dynamic kinetic aza-Michael addition: Stereoselective synthesis of imidazolidin-4-ones

(Figure Presented) In control: An α-amino amide reacted with an aldehyde and a Michael acceptor to form stable imidazolidin-4-ones with high stereoselectivity. A dynamic kinetic aza-Michael addition was discovered and applied to the three-component reacti