17916-88-0

Basic information

• Product Name: AC-D-VAL-OH
• Synonyms: AC-D-VALINE;AC-D-VAL-OH;ACETYL-D-VALINE;N-ALPHA-ACETYL-D-VALINE;N-ACETYL-D-VAL;N-ACETYL-D-VALINE;(R)-2-ACETYLAMINO-3-METHYL-BUTYRIC ACID;N-acetyl-D-valine sigma gr
• CAS NO: 17916-88-0
• Molecular Formula: C₇H₁₃NO₃
• Molecular Weight: 159.18
• EINECS: 241-860-9
• Product Categories: Amino Acid Derivatives;Amino Acids;Ac-Amino Acids;Amino Acids (N-Protected);Biochemistry
• Mol File: 17916-88-0.mol

Chemical Properties

• Melting Point: 167-169℃
• Boiling Point: 362.164 °C at 760 mmHg
• Flash Point: 172.831 °C
• Appearance: /Solid
• Density: 1.095 g/cm³
• Vapor Pressure: 3.14E-06mmHg at 25°C
• Refractive Index: -12 ° (C=1, AcOH)
• Storage Temp.: −20°C
• Solubility: almost transparency in Acetic acid
• PKA: 3.62±0.10(Predicted)
• CAS DataBase Reference: AC-D-VAL-OH(CAS DataBase Reference)
• NIST Chemistry Reference: AC-D-VAL-OH(17916-88-0)
• EPA Substance Registry System: AC-D-VAL-OH(17916-88-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-43
• Safety Statements: 26-36/37
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 17916-88-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
AC-D-VAL-OH is used as an intermediate for the microbial production of D-amino acids and their derivatives, which are essential components in the synthesis of various pharmaceutical compounds. These D-amino acids and their derivatives have potential applications in the development of new drugs and therapeutic agents.
Used in Microbial Production:
AC-D-VAL-OH is used as a key intermediate in the microbial production process, enabling the efficient synthesis of D-amino acids and their derivatives. This process is an environmentally friendly and sustainable approach to producing these valuable compounds, which can be further utilized in various applications across different industries.

InChI:InChI=1/C7H13NO3/c1-4(2)6(7(10)11)8-5(3)9/h4,6H,1-3H3,(H,8,9)(H,10,11)

Upstream product

• 516-06-3 D,L-valine 
• 830-03-5 4-nitrophenol acetate 
• 52152-47-3 N-acetyl-DL-valine methyl ester 
• 6642-21-3 2-acetylamino-3-methyl-crotonic acid 
• 64724-68-1 diethyl 2-N-acetylamino-2-isopropylmalonate 
• 96-81-1 N-acetyl-D,L-valine 
• 17623-72-2 2-methyl-4-iso-propyl-4H-oxazolin-5-one 
• 194661-10-4 propyl N-acetyl-valinate 
• 194661-11-5 N-Acetyl-D,L-valin-n-butylester 
• 56430-36-5 (RS)-N-acetyl valine ethyl ester 
• 96574-46-8 N²-<(R)-N²-acetylvalyl>-L-phenylalanine dimethylamide 
• 640-68-6 D-Val-OH 
• 108-24-7 acetic anhydride 
• 72-18-4 L-valine 

Downstream Products

• 17623-72-2 2-methyl-4-iso-propyl-4H-oxazolin-5-one 
• 109924-94-9 Ac-(R,S)-Val-(R,S)-PhSer-OMe 
• 114285-08-4 C₇H₁₂NO₃ 
• 72-18-4 L-valine 
• 923954-52-3 N-acetyl-ambo-valyl-ambo-alanine methyl ester 
• 251988-77-9 N-[2-methyl-1-(4-methyl-benzoyl)-propyl]-acetamide 
• 96-81-1 N-acetyl-L-valine 
• 96574-46-8 N²-<(R)-N²-acetylvalyl>-L-phenylalanine dimethylamide 
• 96574-45-7 N²-<(S)-N²-acetylvalyl>-L-phenylalanine dimethylamide 
• 1072014-00-6 C₂₄H₃₄N₂O₆ 
• 1072014-01-7 C₂₄H₃₄N₂O₆ 
• 76718-84-8 2-[4-(N-acetyl-D-valylamino)phenyl]-4-hydroxy-5-pyrimidine carboxylic acid 
• 1394018-10-0 N-(3-methyl-1-(4-nitrophenyl)-1-oxobutan-2-yl)acetamide 
• 110409-07-9 Ac-(R,S)-Val-(R,S)-PhSer-OH 

Relevant articles and documents

Reactivity of α-Amino Acids in the Reaction with Esters in Aqueous–1,4-Dioxane Media

The kinetics of the reaction of a series of α-amino acids with 4-nitrophenyl acetate, 4-nitrophenyl benzoate, and 2,4,6-trinitrophenyl benzoate in aqueous 1,4-dioxane medium has been studied. Kinetics of the reactions involving 4-nitrophenyl acetate and 2,4,6-trinitrophenyl benzoate has complied with the Br?nsted dependence and revealed linear correlation between rate constant logarithm and the energy difference of the frontier orbitals of α-amino acids anions.

Formation and hydrolysis of amide bonds by lipase A from Candida antarctica; Exceptional features

Various commercial lyophilized and immobilized preparations of lipase A from Candida antarctica (CAL-A) were studied for their ability to catalyze the hydrolysis of amide bonds in N-acylated α-amino acids, 3-butanamidobutanoic acid (β-amino acid) and its ethyl ester. The activity toward amide bonds is highly untypical of lipases, despite the close mechanistic analogy to amidases which normally catalyze the corresponding reactions. Most CAL-A preparations cleaved amide bonds of various substrates with high enantioselectivity, although high variations in substrate selectivity and catalytic rates were detected. The possible role of contaminant protein species on the hydrolytic activity toward these bonds was studied by fractionation and analysis of the commercial lyophilized preparation of CAL-A (Cat#ICR-112, Codexis). In addition to minor impurities, two equally abundant proteins were detected, migrating on SDS-PAGE a few kDa apart around the calculated size of CAL-A. Based on peptide fragment analysis and sequence comparison both bands shared substantial sequence coverage with CAL-A. However, peptides at the C-terminal end constituting a motile domain described as an active-site flap were not identified in the smaller fragment. Separated gel filtration fractions of the two forms of CAL-A both catalyzed the amide bond hydrolysis of ethyl 3-butanamidobutanoate as well as the N-acylation of methyl pipecolinate. Hydrolytic activity towards N-acetylmethionine was, however, solely confined to the fractions containing the truncated form of CAL-A. These fractions were also found to contain a trace enzyme impurity identified in sequence analysis as a serine carboxypeptidase. The possible role of catalytic impurities versus the function of CAL-A in amide bond hydrolysis is further discussed in the paper. The Royal Society of Chemistry 2010.

Amidoearbonylation of aldehydes utilizing cobalt oxide-supported gold nanoparticles as a heterogeneous catalyst

Cobalt oxide-supported gold-nanoparticles-catalyzed transformation of aldehydes and their equivalents to N-acyl-α-arnino acids was achieved. The desired products were obtained in moderate to excellent yields under milder reaction conditions than previous reports employing octacarbonyldicobalt as a catalyst. Copyright

Microwave-assisted synthesis of amide under solvent-free conditions

An efficient and environmentally friendly synthetic method for the synthesis of primary amides under microwave irradiation was described, in which the primary amine was directly reacted with acid without any catalytic agents. The reaction took place in 8-12-min, which was much shorter than the traditional synthetic methods, with almost quantitative yields. The influential factor of the reaction was discussed. The tautomerization between the carboxylic acid group and the H atom in α-carbon of L-amino acid was observed, presumably a dehydrated intermediate forming from this tautomerized isomer. Copyright Taylor & Francis Group, LLC.

Novel phosphine ligands

The invention is concerned with new phosphine ligands of the formula I wherein R1 and R2 are independently of each other alkyl, aryl, cycloalkyl or heteroaryl, said alkyl, aryl, cycloalkyl or heteroaryl may be substituted by alkyl, alkoxy, halogen, hydroxy, amino, mono- or dialkylamino, aryl, —SO2—R7, —SO3?, —CO—NR8R8′, carboxy, alkoxycarbonyl, trialkylsilyl, diarylalkylsilyl, dialkylarylsilyl or triarylsilyl; R3 is alkyl, cycloalkyl, aryl or heteroaryl; R4′ and R4 signify independently of each other hydrogen, alkyl or optionally substituted aryl; or R4′ and R4 together with the C-atom they are attached to form a 3-8-membered carbocyclic ring; dotted line is absent or is present and forms a double bond; R5 and R6 are independently of each other hydrogen, alkyl or aryl; or linked together to form a 3-8-membered carbocyclic ring or an aromatic ring; R7 is alkyl, aryl or NR8R8′; and R8 and R8′ are independently of each other hydrogen, alkyl or aryl; metal complexes with such ligands as well as the use of such metal complexes as catalysts in asymmetric reactions.

Palladium-catalyzed amidocarbonylation improved by recyclable ionic liquids

Two types of ionic liquids (halide anion ionic liquids and Brensted acidic ionic liquids) were first applied to improve the palladium-catalyzed amidocarbonylation. Both the palladium catalyst and the ionic liquids could be recycled at least five times without significant loss in catalytic activity. Georg Thieme Verlag Stuttgart.

A study of amidocarbonylation reactions catalyzed by Pd/HZSM-5

A HZSM-5-supported palladium catalyst, which was prepared by the conventional impregnation method, was utilized in amidocarbonylation reactions. Several important parameters were optimized to give moderate to excellent yields. The catalyst recycling of Pd/HZSM-5, for the first time, was achieved for at least four run times without depreciation of catalytic activity. The studies of TEM images revealed that agglomeration of the palladium species of Pd/ HZSM-5 catalyst was avoided after reaction, which was quite different from the case of Pd/C catalyst.

METHOD OF AMIDOCARBONYLATION REACTION

A novel method of an amidocarbonylation reaction among an aldehyde compound, an amide compound, and carbon monoxide, which comprises using a palladium-supporting crosslinked-polymer composition containing palladium clusters having a major-axis length of 20 nm or shorter to conduct the amidocarbonylation reaction. Thus, an N-acyl-±-amino acid can be more efficiently and selectively synthesized in a clean reaction system. Also provided is a catalyst for use in the method.

Efficient synthesis of N-acyl-α-amino acids via polymer incarcerated palladium-catalyzed amidocarbonylation

A novel polymer incarcerated Pd catalyst (PI Pd 7c) was synthesized from amide-containing polymer 6b, and this catalyst was shown to be effective in amidocarbonylation, which is a versatile one-pot method for the preparation of N-acyl-α-amino acids. The reactions proceeded smoothly with a wide variety of substrates, and no leaching of the Pd metal to the reaction mixture was detected.

Platinum-catalyzed amidocarbonylation

The first example of platinum-catalyzed amidocarbonylation of aldehydes with amides and carbon monoxide is described. In contrast to precedent palladium catalysis, a remarkable ligand acceleration by phosphines was observed. Furthermore, an optically active N-acetyl amino acid was partially epimerized under the platinum-catalyzed conditions, while faster racemization was observed under the palladium catalysis.