1219-46-1

Usage

Chemical Properties

white to beige powder

InChI:InChI=1/C13H18N2O3/c14-11(13(17)18)8-4-5-9-15-12(16)10-6-2-1-3-7-10/h1-3,6-7,11H,4-5,8-9,14H2,(H,15,16)(H,17,18)/t11-/m0/s1

Upstream product

• 56-87-1 L-lysine 
• 98-88-4 benzoyl chloride 
• 5107-18-6 N⁶-benzoyl-lysine 
• 89305-51-1 N⁶-benzoyl-DL-lysine amide; hydrochloride 
• 70326-37-3 phenyl(2-thioxothiazolidin-3-yl)methanone 
• 32513-92-1 Nα,ε-dibenzoyl-D,L-lysine 
• 109036-22-8 N⁶-benzoyl-N²-butyryl-DL-lysine 
• 109454-36-6 N⁶-benzoyl-N²-chloroacetyl-DL-lysine 
• 3066-80-6 N²-acetyl-N⁶-benzoyl-DL-lysine 
• 14609-03-1 6-benzoylamino-2-tert-butoxycarbonylamino-hexanoic acid 
• 99532-86-2 N,2-[(1,1-dimethylethoxy)carbonyl]-L-lysine methyl ester hydrochloride 

Downstream Products

• 1700-05-6 (S)-2-bromo-6-benzamino-hexanoic acid-⁽¹⁾ 
• 883721-36-6 N^α-benzenesulfonyl-N^ε-benzoyl-L-lysine 
• 98352-77-3 N⁶-benzoyl-N²-(toluene-4-sulfonyl)-L-lysine 
• 24696-20-6 N^α-(2.4-dinitro-phenyl)-L-lysine 
• 326-51-2 N⁶-benzoyl-N²-trifluoroacetyl-L-lysine 
• 79251-84-6 N^ε-benzoyl-L-lysine methyl ester hydrochloride 
• 47086-64-6 4-(4-benzoylaminobutyl)oxazolidine-2,5-dione 
• 65-85-0 benzoic acid 
• 14609-03-1 6-benzoylamino-2-tert-butoxycarbonylamino-hexanoic acid 
• 7431-89-2 N^α-Methyl-L-lysin 
• 98352-78-4 N⁶-benzoyl-N²-methyl-N²-(toluene-4-sulfonyl)-L-lysine 
• 908575-98-4 N^ε-benzoyl-N^α-benzyloxycarbonyl-L-lysine hydrazide 
• 168974-62-7 N²-benzenesulfonyl-L-lysine 
• 2104-87-2 N²-(toluene-4-sulfonyl)-L-lysine 

Relevant academic research and scientific papers

Process Development of a Second Generation β-Amyloid-Cleaving Enzyme Inhibitor - Improving the Robustness of a Halogen-Metal Exchange Using Continuous Stirred-Tank Reactors

Process development for the synthesis of a second generation β-amyloid-cleaving enzyme (BACE1) inhibitor (1) is described. The lithiothiazole addition to the isoxazolene (5) under batch conditions was not scalable because of reaction gelling and anion instability. A continuous stirred-tank reactor flow process was developed and successfully executed on the 70 kg scale in multiple runs. In a head-to-head comparison between the continuous and batch processes, the former was clearly superior as it gave a higher yield (80 vs 63%) of the adduct (4) and better reaction control for handling the unstable lithiothiazole as a reaction intermediate. Subsequently, 4 underwent Pd-catalyzed amination with t-butyl carbamate, reductive cleavage of the N-O bond, thioamidine cyclization, and deprotection of the Boc group to provide hydropyranothiazine 2. The synthesis of 1 was completed by amidation with 5-(difluoromethoxy)picolinic acid and the successive deprotection of the benzamide group with either Silicycle-diamine or l-lysine.

The Effects of Prodrug Size and a Carbonyl Linker on l-Type Amino Acid Transporter 1-Targeted Cellular and Brain Uptake

The l-type amino acid transporter 1 (LAT1, SLC7A5) imports dietary amino acids and amino acid drugs (e. g., l-DOPA) into the brain, and plays a role in cancer metabolism. Though there have been numerous reports of LAT1-targeted amino acid-drug conjugates (prodrugs), identifying the structural determinants to enhance substrate activity has been challenging. In this work, we investigated the position and orientation of a carbonyl group in linking hydrophobic moieties including the anti-inflammatory drug ketoprofen to l-tyrosine and l-phenylalanine. We found that esters of meta-carboxyl l-phenylalanine had better LAT1 transport rates than the corresponding acylated l-tyrosine analogues. However, as the size of the hydrophobic moiety increased, we observed a decrease in LAT1 transport rate with a concomitant increase in potency of inhibition. Our results have important implications for designing amino acid prodrugs that target LAT1 at the blood-brain barrier or on cancer cells.

(2,5-DIOXOIMIDAZOLIDIN-I-YL)-N-HYDROXY-ACETAMIDES AS METALLOPROTEINASE INHIBITORS

The invention provides compounds of the formula (I) wherein the variables are as defined in the specification. The compounds of the invention are inhibitors of metalloproteinase MMP-12 and are among other things useful for the treatment of obstructive air

Decomposition of copper-amino acid complexes by sodium sulfide

Sodium sulfide very efficiently removes copper from protected amino acid-copper complexes. The copper in the amino acid complex was reduced to insoluble cuprous sulfide and the free amino acid was released in pure form. This method is very convenient and rapid, requiring only 5-10 min and 0.55-0.75 equiv of sodium sulfide.

Peptide-bond Formation, Chemoselective Acylation of Amino Acids, and Crosslinking Reaction between Amino Acids Utilizing a Functional Five-membered Heterocycle, 1,3-Thiazolidine-2-thione

The monitored aminolysis of 3-acyl-1,3-thiazolidine-2-thiones has been extended to the peptide-bond formation, the chemoselective acylation of amino acids having multifunctional groups, and the crosslinking reaction between amino acids.

MONITORED AMINOLYSIS OF 3-ACYL-1,3-THIAZOLIDINE-2-THIONE WITH AMINO ACID AND ITS DERIVATIVE: PEPTIDE BOND FORMATION, CHEMOSELECTIVE ACYLATION, AND BRIDGING REACTION

As a new extention of the monitored aminolysis of 3-acyl-1,3-thiazolidine-2-thione, its applications to peptide bond formation, chemoselective acylation of amino acid, and bridging reaction on the enzyme model are reported.