19764-30-8

Basic information

• Product Name: N-Acetyl-D-leucine
• Synonyms: 2-Acetylamino-4-methylvaleric acid;N-Acetyl-2-isobutylglycine;D-2-Acetylamino-4-methylvaleric acid;2,N-Acetyl-D-leucine;(R)-2-acetaMido-4-Methylpentanoic acid;D-Leucine, N-acetyl-;N-Ac-D-Leu-OH;(R)-Ac-2-amino-4-methylpentanoic acid
• CAS NO: 19764-30-8
• Molecular Formula: C₈H₁₅NO₃
• Molecular Weight: 173.21
• EINECS: 1533716-785-6
• Product Categories: Amino Acids;Modified Amino Acids;amino acid;Amino ACIDS SERIES;chiral;Amino Acids;Leucine [Leu, L];Ac-Amino Acids;Amino Acids (N-Protected);Biochemistry;N-Acetyl-Amino acid series;A - H
• Mol File: 19764-30-8.mol

Chemical Properties

• Melting Point: 176-177C
• Boiling Point: 369.7 °C at 760 mmHg
• Flash Point: 177.4 °C
• Appearance: /
• Density: 1.069 g/cm³
• Refractive Index: 23 ° (C=4, EtOH)
• Storage Temp.: −20°C
• Solubility: DMSO (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly)
• PKA: 3.67±0.10(Predicted)
• CAS DataBase Reference: N-Acetyl-D-leucine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Acetyl-D-leucine(19764-30-8)
• EPA Substance Registry System: N-Acetyl-D-leucine(19764-30-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 19764-30-8(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white powder

Upstream product

• 57289-25-5 methyl N-acetyl-leucinate 
• 915008-30-9 2-acetylamino-4-methyl-pent-2-enoic acid 
• 64896-30-6 (Z)-2-Acetylamino-4-methyl-pent-2-enoic acid 
• 328-38-1 (R)-leucine 
• 830-03-5 4-nitrophenol acetate 
• 2256-97-5 N-acetyl-DL-isoleucine butyl ester 
• 60-35-5 acetamide 
• 201230-82-2 carbon monoxide 
• 590-86-3 isovaleraldehyde 
• 99-15-0 N-acetylleucine 

Downstream Products

• 328-38-1 (R)-leucine 
• 187345-48-8 (R)-2-Acetylamino-4-methyl-pentanoic acid ((R)-3-benzyl-1-benzyloxy-2,5-dioxo-pyrrolidin-3-yl)-amide 
• 221685-11-6 (R)-2-Acetylamino-4-methyl-pentanoic acid ((S)-3-benzyl-1-benzyloxy-2,5-dioxo-pyrrolidin-3-yl)-amide 
• 187345-49-9 (+)-(3R)-3-(N-acetyl-D-leucylamino)-3-benzyl-1-hydroxysuccinimide 
• 876290-45-8 (R)-tetrahydropapaverine-N-acetyl-D-leucine salt 
• 608142-28-5 (R)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethylamine N-acetyl-D-leucine salt 
• 909122-82-3 potassium N-acetyl-D-leucine salt 
• 374926-58-6 1-(R)-1-(2,3-dihydrobenzofuran-5-yl)-2-benzyl-2,3,4,9-tetrahydro-1H-β-carboline 

Relevant articles and documents

Development of a high throughput screening tool for biotransformations utilising a thermophilic l-aminoacylase enzyme

Micro-reactors containing a monolith-immobilised thermophilic l-aminoacylase, from Thermococcus litoralis, have been developed for use in biotransformation reactions and a study has been carried out to investigate the stereospecificity and stability of the immobilised enzyme. The potential to use the developed micro-reactors as a tool for rapid screening of enzyme specificity was demonstrated, confirming that the l-aminoacylase showed a similar substrate specificity to that previously reported of the free enzyme. From this baseline, the technique was employed as a tool to evaluate potential unreported substrates with N-benzoyl- (l-threonine, l-leucine and l-arginine) and N-acetyl- (d,l-serine, d,l-leucine, l-tyrosine and l-lysine) protecting groups. The order of preferred substrates was found to be Phe > Thr > Leu > Arg for N-benzoyl substrates and Phe ? Ser > Leu > Met > Tyr > Trp for N-acetyl substrates. It was found that by using the micro-reactor a significantly smaller quantity of enzyme and substrates was required. It was shown that the micro-reactors were still operational in the presence of selected organic solvents, such as ethanol, methanol, acetone, dimethylformamide (DMF) and dimethylsulfoxide (DMSO). The results indicated that a combination of a small amount of an appropriate solvent (5% DMSO) and a higher reaction temperature could be employed in biotransformations where substrate solubility was an issue.

Efficient chemoenzymatic synthesis of enantiomerically pure α-amino acids

A general two-step chemoenzymatic synthesis for enantiomerically pure natural and nonnatural α-amino acids is presented. In the first step of the sequence, the ubiquitous educts aldehyde, amide and carbon monoxide react by palladium-catalyzed amidocarbonylation to afford the racemic N-acyl amino acids in excellent yields. In the second step, enzymatic enantioselective hydrolysis yields the free optically pure a-amino acid and the other enantiomer as the N-acyl derivative, both in optical purities of 85-99.5% ee. The advantage of the chemoenzymatic process compared to other amino acid synthesis are demonstrated by the preparation of various functionalized (-OR, -Cl, -F, -SR) α-amino acids on a 10-g scale.

Enantioselective hydrolytic reactions of rice bran lipase (RBL): A first report

Enantioselectivity has been observed in the hydrolysis of racemic N-acetyl amino acid esters with rice bran lipase (RBL). The enzyme shows selectivity towards the (S)-enantiomer. Products with high enantiomeric excess (e.e. >99%) are obtained depending upon the hydrophobicity of the amino acid as well as that of the leaving group.

Selectivity in Carbonic Anhydrase Catalyzed Hydrolysis of Standard N-Acetyl-DL-amino Acid Methyl Esters

Carbonic anhydrase-catalyzed hydrolysis of some standard N-acetyl-DL-amino acid methyl esters proceeds with high enantioselectivity.This enzyme hydrolyses selectively D amino acid derivatives in contrast to proteases which have a L stereoselectivity. Key Words: carbonic anhydrase, hydrolysis, N-acetyl-DL-amino acid methyl esters, enantioselectivity.

Catalysis by β-cyclodextrin in the reaction of p-nitrophenyl acetate with α-amino acids

The reactions of p-nitrophenyl acetate, 1, with both enantiomers of the following α-amino acids: alanine (2a), methionine (2b), leucine (2c), and tryptophan (2d), were studied in the presence of β-cyclodextrin (β-CD).All the reactions were catalyzed by β-

Efficient Asymmetric Hydrogenations of (Z)-2-Acetamidoacrylic Acid Derivatives with the Cationic Rhodium Complex of (2S,4S)-MOD-BPPM

The preparation of (2S,4S)-MOD-BPPM ((2S,4S)-N-(t-butoxycarbonyl)-4-phosphino>-2-phosphino>methyl>pyrrolidine) and its application to highly effective asymmetric hydrogenations of (Z)-2-acetamidoacrylic acid derivatives are described.

Kinetic Resolution of Unnatural and Rarely Occuring Amino Acids: Enantioselective Hydrolysis of N-Acyl Amino Acids Catalyzed by Acylase I

Acylase I (aminoacylase; N-acylamino-acid amidohydrolase, EC 3.5.1.14, from porcine kidney and the fungus Aspergillus) is broadly applicable enzymatic catalyst for the kinetic resolution of unnatural and rarely occuring α-amino acids.Its enantioselectivity for the hydrolysis of N-acyl L-α-amino acids is nearly absolute, yet it accepts substrates having a wide range of structure and functionality.This paper reports the initial rates of enzyme-catalyzed hydrolysis of over 50 N-acyl amino acids and analogues, the stabilities of the enzymes in aqueous and aqueous/organic solutions, and the effects of different acyl groups and metal ions on the rates of enzymatic hydrolysis.Eleven α-amino and α-methyl α-amino acids were resolved on a 2-29-g scale.Crude L- and D-amino acid products had generally >90percent ee.The utility of resolved amino acids as chiral synthons was illustrated by the preparation of (R)- and (S)-1-butene oxide and the diastereoselective (cis:trans, 7-8:1) iodolactonization of three 2-amino-4-alkenoic acid derivatives.

O.N-Bis(diphenylphosphino) Derivatives of Chiral trans- and cis-2-Aminocyclohexanols: Synthesis and Enantioselective Behaviour as Ligands in Rh-based Homogeneous Hydrogenation Catalysts

trans- and cis-2-Methylamino cyclohexanols (MAC) were prepared in enantiomerically pure forms and transformed into O.N-bis(diphenylphosphino) derivatives ("PONP").An analogous trans-1R;2R-aminocyclohexanol PONP could only be isolated in an impure form, whereas the attempted synthesis of PONP's of diastereomeric trans-2-(N-α-phenylethylamino)-cyclohexanols failed.Cationic Rh(I)-chelates of the new PONP's catalyzed the enantioselective hydrogenation of dehydro-α-acylamino acids with /= 97percent ee.A comparison of the enantiodiscriminating properties of the MAC-PONP's with structurally related chiral ligands leads to surprising conclusions.

Asymmetric Hydrogenation Catalyzed by Rhodium Complex with a New Chiral Bisphosphine Derived from L-Threonine

A new chiral bisphosphine, (2R,3S)-1,2-bis(diphenylphosphino)-3-'Boc-aminobutane (RS-5), was prepared from L-threonine.Mesylation of 'Boc-L-threonine methyl ester (2) and subsequent reduction with sodium borohydride gave the alcohol (10), which was treated with potassium carbonate to afford a key intermediate, (2S,3S)-1-'Boc-3-methyl-2-aziridinemethanol (SS-7b).Mesylation of SS-7b, followed by treatment with sodium diphenylphosphide afforded the new chiral bisphosphine (RS-5).The structure of RS-5 was confirmed by the X-ray analysis of its crystalline CuCl complex (RS-12).The cationic rhodium (I) complexes prepared from RS-5 and RS-12 are efficient asymmetric hydrogenation catalysts for N-acyldehydroamino acids, giving (S))-N-acylamino acids in high optical yields (83-94percentee).