4434-61-1

Basic information

• Product Name: N-CARBOBENZOXY-DL-METHIONINE
• Synonyms: Z-DL-METHIONINE;Z-DL-MET-OH;CBZ-DL-MET-OH;2-BENZYLOXYCARBONYLAMINO-4-METHYLSULFANYL-BUTYRIC ACID;Carbobenzoxymethionine;N-benzyloxycarbonyl-DL-methionine;N-CBZ-DL-Methionine N-Carbobenzyloxy-DL-methionine;Z-DL-MET
• CAS NO: 4434-61-1
• Molecular Formula: C₁₃H₁₇NO₄S
• Molecular Weight: 283.34
• EINECS: 224-640-7
• Product Categories: Z-Amino Acids and Derivatives;Amino Acids;Amino Acids (N-Protected);Biochemistry;Cbz-Amino Acids
• Mol File: 4434-61-1.mol

Chemical Properties

• Melting Point: 113 °C
• Boiling Point: 504.7 °C at 760 mmHg
• Flash Point: 259 °C
• Appearance: /
• Density: 1.253 g/cm³
• Vapor Pressure: 6.58E-14mmHg at 25°C
• Refractive Index: 1.59
• Storage Temp.: -20°C
• Solubility: almost transparency in Methanol
• CAS DataBase Reference: N-CARBOBENZOXY-DL-METHIONINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-CARBOBENZOXY-DL-METHIONINE(4434-61-1)
• EPA Substance Registry System: N-CARBOBENZOXY-DL-METHIONINE(4434-61-1)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 4434-61-1(Hazardous Substances Data)

Usage

Chemical Properties

White crystalline

InChI:InChI=1/C13H17NO4S/c1-9(16)14-11(13(17)18)8-19-12(7-15)10-5-3-2-4-6-10/h2-6,11-12,15H,7-8H2,1H3,(H,14,16)(H,17,18)/t11-,12?/m0/s1

Upstream product

• 501-53-1 benzyl chloroformate 
• 59-51-8 DL-methionine 
• 16874-01-4 Z-Met-O-tBu 
• 64-17-5 ethanol 
• 348-67-4 D-methionine 
• 921-01-7 rac-cysteine 
• 62-53-3 aniline 
• 127862-75-3 2-Benzyloxycarbonylamino-4-methylsulfanyl-butyric acid 2,2,2-trifluoro-ethyl ester 

Downstream Products

• 122389-49-5 2-(N-benzyloxycarbonyl-methionyloxy)-benzoic acid benzyl ester 
• 1152-62-1 (2R)-2-[[(benzyloxy)carbonyl]amino]-4-(methylsulfanyl)butanoic acid 
• 95277-61-5 (S)-benzyl 4-(methylthio)-1-oxo-1-(phenylamino)butan-2-ylcarbamate 
• 96976-97-5 {1-[Bis-(2-chloro-ethyl)-carbamoyl]-3-methylsulfanyl-propyl}-carbamic acid benzyl ester 
• 83972-33-2 N-<(benzyloxy)carbonyl>-DL-methionine methyl ester 
• 113718-97-1 L-Z-Met-OEt 
• 121335-14-6 2-Benzyloxycarbonylamino-4-methylsulfanyl-butyric acid 6-nitro-benzotriazol-1-yl ester 
• 1152-62-1 Cbz-Met-OH 
• 87023-92-5 N-benzyloxycarbonyl-DL-methionyl-(3,5-dimethyl)pyrazole 
• 3611-20-9 N-benzyloxycarbonyl-methionine-[2]naphthylamide 
• 127862-75-3 2-Benzyloxycarbonylamino-4-methylsulfanyl-butyric acid 2,2,2-trifluoro-ethyl ester 
• 711017-03-7 tert-butyl (2S)-2({N-[(benzyloxy)carbonyl]-L-methionyl}amino)butanoate 
• 711017-05-9 tert-butyl N-[(benzyloxy)carbonyl]-L-methionyl-L-phenylalaninate 
• 79635-49-7 5'-O-(N-benzyloxycarbonylmethionyl)-5-fluorouridine 

Relevant articles and documents

Symmetric benzidine derivatives as anti-HCV agents: Insight into the nature, stereochemistry of the capping amino acid and the size of the terminal capping carbamates

Novel symmetric molecules, bearing a benzidine prolinamide core, two terminal carbamate caps of variable sizes and nature, including natural and unnatural amino acids were developed. Several terminal N-carbamate substituents of the core structure, ranging from linear methyl, ethyl and butyl groups to branching isobutyl group; and an aromatic substituent were also synthesized. Series 1 has hydrophobic AA residues, namely S and R phenylglycine and a terminal carbamate capping group, whereas Series 2 bears sulphur containing amino acids, specifically S and R methionine and the natural R methylcysteine. The novel compounds were tested for their inhibitory activity (EC50) and their cytotoxicity (CC50), using an HCV 1b (Con1) reporter replicon cell line. Compound 4 with the unnatural capping residue, bearing D-Phenylglycine amino acid residue and N-isobutyloxycarbonyl capping group, was the most active within the two series, with EC50 = 0.0067 nM. Moreover, it showed high SI50 > 14788524 and was not cytotoxic at the highest tested concentration (100 μΜ), indicating its safety profile. Compound 4 also inhibited HCV genotypes 2a, 3a and 4a. Compared to the clinically approved NS5A inhibitor Daclatasvir, compound 4 shows higher activity against genotypes 1b and 3a, as well as improved safety profile.

Enantioselective inclusion of pyrene-1-sulfonate salts of α-amino acids with crystals of α-cyclodextrin

Enantioselective inclusion of α-amino acids with crystals of α-cyclodextrin (α-CD) has been achieved by converting the amino acids into sulfonate salts with pyrene-1-sulfonic acid (PyS). For example, crystals of α-CD selectively include L-leucine/PyS (1:1) salt in a host/guest ratio of ～1 with 92%ee from a solution of the racemic salt in ethanol/N-methylformamide (91:9) at 40 °C. Under conditions optimized for individual amino acids, the PyS salts of valine, phenylalanine, and methionine are also included with good enantioselectivities (up to 86%ee). Mechanistic studies for the inclusion of leucine/PyS salt reveals that the enantioselectivity originates from the difference in stability between the inclusion complexes of D- and L-leucine/PyS salts with α-CD in crystals.

POLYCYCLIC TLR7/8 ANTAGONISTS AND USE THEREOF IN THE TREATMENT OF IMMUNE DISORDERS

The present invention relates to compounds of Formula (I) and pharmaceutically acceptable compositions thereof, useful as toll-like receptor 7/8 (TLR7/8) antagonists. In Formula (I), Ring A is aryl or heteroaryl; Ring B is aryl or heteroary; and X is C(R4)2, O, NR4, S, S(R4), or S(R4)2.

Resolution of non-protein amino acids via Carica papaya lipase-catalyzed enantioselective transesterification

Carica papaya lipase-catalyzed transesterification of the 2,2,2-trifluoroethyl esters of N-benzyloxycarbonylated dl-amino acids carrying aliphatic side chains proceeded smoothly and, in almost all the cases, enantiospecifically (E = >200), affording the l-methyl esters and leaving the d-trifluoroethyl esters intact.

Cyclic hydroxamates, especially multiply substituted [1,2]oxazinan-3-ones

Routes to putative N-acyl-D-ala-D-ala surrogates, beginning with the conversion of 4-, 5-, and 6-membered lactones into 5-, 6-, and 7-membered cyclic hydroxamates, are reported. The key step of the synthesis is trimethylaluminium-promoted cyclization of an ω-aminooxyester. The 7-membered cyclic hydroxamate crystallizes in a chair conformation. Extension of the reaction sequence to homoserine or homoserine lactone leads to cyclocanaline and N-acylated cyclocanalines. The 4-phenylacetamido derivative of cyclocanaline crystallizes in a boat conformation. The attachment of a 2-carboxypropyl substituent to the ring nitrogen of a 4-acylaminocyclocanaline has been effected, prior to cyclization, by coupling of the acyclic aminooxyester precursor to the triflate of benzyl lactate or, after cyclization, by coupling to tert-butyl α-bromopropionate in the presence of potassium fluoride - alumina, followed by removal of the protecting group in each case. A six-membered homolog of the antibiotic lactivicin has been synthesized by the reaction of 4-phenylacetamidocyclocanaline with benzyl 2-oxoglutarate in the presence of carbodiimide, followed by hydrogenolysis. Starting with methyl 2,4-dibromo-2,4-dideoxy-L-erythronate, which is available in two steps from L-ascorbic acid, these reaction sequences have been applied to the stereospecific synthesis of a D-alanine derivative whose nitrogen atom is enclosed within a 3,4-disubstituted [1,2]oxazinan-3-one.

Highly selective deprotection of tert-butyl esters using ytterbium triflate as a catalyst under mild conditions

Ytterbium triflate catalyses the deprotection of tert-butyl esters selectively in the presence of other esters under mild conditions in almost quantitative yields. The reactions are carried out in nitromethane (45°-50°C) using 5 mole percent of the catalyst.

Insecticidal Properties of Some Derivatives of L-Canavanine

The canavanine derivatives D-canavanine and L-homocanavanine as well as the 1-methyl and 1-ethyl esters of L-canavanine were synthesized and evaluated for biological activity in fifth instar larvae of the tobacco hornworm, Manduca sexta .While L-homocanavanine did not increase intrinsic toxicity, it was as deleterious as L-canavanine.D-Canavanine was biologically active, as demonstrated by its ability to cause larval edema, but the D-enantiomer had little ability to elicit the larval growth inhibition and pupal deformity which are hallmarks of canavanine toxicosis and was postulated to be linked to aberrant protein production.The 1-methyl and 1-ethyl esters of L-canavanine were synthesized to determine if enhancing canavanine's hydrophobicity might increase its bioavailability.Our experiments revealed that these esters are less toxic than canavanine; the ethyl ester disrupted larval growth more than did the methyl analogue. - Keywords: L-Canavanine; D-canavanine; L-homocanavanine; 1-methyl-L-canavanine; 1-ethyl-L-canavanine; Manduca sexta

Structure and Stereochemistry of Three Phytotoxins, Syringomycin, Syringotoxin and Syringostatin, Produced by Pseudomonas syringae pv. syringae

The structures of two phytotoxins, syringomycin and syringotoxin, produced by Pseudomonas syringae pv. syringae, were determined.Several amino acid residues of syringomycin were different from those in the syringostatins.Syringotoxin B proved to be syringostatin A.The three kinds of phytotoxins showed close structural similarity, and the stereochemistry of their components was deduced and compared.

Porcine Pancreatic Lipase Catalyzed Enantioselective Hydrolysis of Esters of N-Protected Unusual Amino Acids

Porcine pancreatic lipase catalyzed the highly enantioselective hydrolysis of a kind of α-substituted carboxylic esters, i.e., the 2,2,2-trifluoroethyl esters of the N-benzyloxycarbonyl derivatives of unusual amino acids.

Direct Optical Resolution of Carboxylic Acids by Chyral HPLC on Tris(3,5-dimethylphenylcarbamate)s of Cellulose and Amylose

A variety of racemic carboxylic acids have been for the first time directly resolved by normal-phase, high-performance liquid chromatography using a hexane-2-propanol eluting system containing a small amount (ca. 1percent) of a strong carboxylic acid, like formic acid, trichloroacetic acid, and trifluoroacetic acid.