67865-68-3

Usage

Uses

Used in Research Applications:
Z-L-Ala-CHN2 is used as a research tool for studying the function and inhibition of proteolytic enzymes. Its potent inhibitory activity makes it valuable in understanding enzyme mechanisms and their role in various biological processes.
Used in Pharmaceutical Development:
Z-L-Ala-CHN2 is used as a potential therapeutic agent for conditions involving excessive protease activity. Its anti-inflammatory properties suggest that it could be a targeted treatment for such conditions, offering a new avenue for drug development.
Used in Enzyme Inhibition Studies:
In the field of biochemistry, Z-L-Ala-CHN2 is used as an enzyme inhibitor to explore the effects of proteolytic enzyme inhibition on cellular processes and disease progression. This application aids in the discovery of new therapeutic strategies for diseases where proteolytic enzymes play a critical role.
Used in Anti-inflammatory Treatments:
Given its demonstrated anti-inflammatory properties, Z-L-Ala-CHN2 is considered for use in anti-inflammatory treatments, particularly for conditions where protease activity contributes to inflammation and tissue damage. This application could lead to more effective treatments with fewer side effects.

Upstream product

• 186581-53-3 diazomethane 
• 65638-93-9 N-Carbobenzoxy-L-alanin-kohlensaeureaethylesteranhydrid 
• 1142-20-7 N-Cbz-Ala 
• 501-53-1 benzyl chloroformate 
• 49760-60-3 N-benzyloxycarbonyl-L-alanyl chloride 
• 25172-67-2 Z-Ala-O-COO-isoBu 

Downstream Products

• 152359-72-3 ((S)-3,3-Dihydroxy-1-methyl-2-oxo-propyl)-carbamic acid benzyl ester 
• 128913-34-8 benzyl (S)-(3-oxo-4-(phenylthio)butan-2-yl)carbamate 
• 83460-84-8 methyl (3S)-3-{[(benzyloxy)carbonyl]amino}butanoate 
• 41036-43-5 (3S)-1-chloro-3-(benzyloxycarbonylamino)-2-butanone 
• 83509-88-0 (S)-3-benzyloxycarbonylaminobutyric acid 
• 155149-62-5 (3-bromo-1-(S)-methyl-2-oxopropyl)carbamic acid benzyl ester 
• 1064162-18-0 (3S,4R,1'S)-3-(1-benzyloxycarbonylaminoethyl)-1-(4-methoxybenzyl)-4-phenylazetidin-2-one 

Relevant academic research and scientific papers

α-Xanthylmethyl Ketones from α-Diazo ketones

A simple and efficient method to obtain α-xanthylmethyl ketones from α-diazo ketones is described. The reaction proceeds through a protonation/nucleophilic substitution sequence in the presence of p -toluenesulfonic acid and potassium ethyl xanthogenate as the nucleophile. As α-diazo ketones can be readily synthesized from ubiquitous carboxylic acids, a broad variety of xanthates can be obtained, including examples from naturally occurring substrates.

Synthesis of enantiopure free and N-benzyloxycarbonyl-protected 3-substituted homotaurines from naturally occurring amino acids

Enantiopure N-benzyloxycarbonyl-protected and free 3-substituted homotaurines were synthesized from naturally occurring amino acids via N-benzyloxycarbonyl protection, Arndt-Eistert homologation, reduction, esterification with thioacetic acid, and oxidation with performic acid. The current method is a convenient, practical, and salt-free method for the synthesis of enantiopure 3-substituted homotaurine with moderate to good yields.

Continuous flow synthesis of β-amino acids from α-amino acids via Arndt-Eistert homologation

A fully continuous four step process for the preparation of β-amino acids from their corresponding α-amino acids utilizing the Arndt-Eistert homologation approach is described. the Partner Organisations 2014.

Synthesis of enantiopure free and N-benzyloxycarbonyl-protected 3-substituted homotaurines from naturally occurring amino acids

Enantiopure N-benzyloxycarbonyl-protected and free 3-substituted homotaurines were synthesized from naturally occurring amino acids via N-benzyloxycarbonyl protection, Arndt-Eistert homologation, reduction, esterification with thioacetic acid, and oxidation with performic acid. The current method is a convenient, practical, and salt-free method for the synthesis of enantiopure 3-substituted homotaurine with moderate to good yields.

Synthesis and anti-Candida activity of novel 2-hydrazino-1,3-thiazole derivatives

Eighteen new hydrazino-1,3-thiazole derivatives were evaluated against 8 strains of multi-resistant Candida spp. Introduction of an indolyl moiety linked to the hydrazone function enhanced the in vitro anti-Candida activity, with an activity spectrum towards Candida albicans strains. Introduction of a (S)-2-aminoethyl chain on the thiazole nucleus largely enhanced the in vitro antifungal activity, with a selectivity oriented towards non-C. albicans species.

1,5-rhodium shift in rearrangement of N -arenesulfonylazetidin-3-ols into benzosultams

Benzosultams are synthesized in an enantiopure form starting from α-amino acids through a rhodium-catalyzed rearrangement reaction of N-arenesulfonylazetidin-3-ols. Mechanistically, this reaction involves C-C bond cleavage by β-carbon elimination and C-H bond cleavage by a 1,5-rhodium shift.

Synthesis of N-urethane protected α-aminoalkyl-α-cyanomethyl ketones; Application to the synthesis of 3-substituted 5-amino-1H-pyrazole tethered peptidomimetics

The preparation of N-protected amino/peptide α-cyanomethyl ketones through cyanation of the corresponding α-bromomethyl ketones is described. The utility of the resulting α-cyanomethyl ketones in the synthesis of 3-substituted-5-amino-1H-pyrazoles has also been demonstrated. In both steps a wide range of N-protected amino/peptide acids has been employed and the products are obtained in good yield. The enantiomeric purity of both the α-cyanomethyl ketones and pyrazoles were confirmed by chiral HPLC analysis of the corresponding Z-protected d- and l-Ala-OH as model substrates. The synthesis of peptide pyrazolecarboxamides is also delineated. Georg Thieme Verlag Stuttgart · New York.

Ultrasound mediated synthesis of 2-amino-1,3-selenazoles derived from Fmoc/Boc/Z-α-amino acids

A simple and efficient one-pot synthesis of Fmoc/Boc/Z-amino acid derived 2-amino-1,3-selenazoles by the condensation of Nα-urethane protected amino acid derived bromomethyl ketones with selenourea under the influence of ultrasound has been described. Insertion of 2-amino-1,3-selenazole moiety in the side chains of Asp and Glu has also been achieved following the similar protocol. ARKAT USA, Inc.

Facile synthesis of optically active imidazole derivatives

Five optically active imidazole derivatives have been synthesized via a facile 4-step reaction sequence starting from commercially available and inexpensive N-Cbz amino acids. While microwave assisted condensation was unsuccessful, the condensation of the

Effective methods for the synthesis of N-methyl β-amino acids from all twenty common α-amino acids using 1,3-oxazolidin-5-ones and 1,3-oxazinan-6-ones

N-Methyl β-amino acids are generally required for application in the synthesis of potentially bioactive modified peptides and other oligomers. Previous work highlighted the reductive cleavage of 1,3-oxazolidin-5-ones to synthesise N-methyl α-amino acids. Starting from α-amino acids, two approaches were used to prepare the corresponding N-methyl β-amino acids. First, α-amino acids were converted to N-methyl α-amino acids by the so-called '1,3-oxazolidin-5-one strategy', and these were then homologated by the Arndt-Eistert procedure to afford N-protected N-methyl β-amino acids derived from the 20 common α-amino acids. These compounds were prepared in yields of 23-57% (relative to N-methyl α-amino acid). In a second approach, twelve N-protected α-amino acids could be directly homologated by the Arndt-Eistert procedure, and the resulting β-amino acids were converted to the 1,3-oxazinan-6-ones in 30-45% yield. Finally, reductive cleavage afforded the desired N-methyl β-amino acids in 41-63% yield. One sterically congested β-amino acid, 3-methyl-3-aminobutanoic acid, did give a high yield (95%) of the 1,3-oxazinan-6-one (65), and subsequent reductive cleavage gave the corresponding AIBN-derived N-methyl β-amino acid 61 in 71% yield (Scheme 2). Thus, our protocols allow the ready preparation of all N-methyl β-amino acids derived from the 20 proteinogenic α-amino acids.