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640-68-6

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640-68-6 Usage

Description

D-valine is the D-form of valine, being the non-proteinogenic isomer of valine. It can be supplemented into the cell culture for selectively inhibition of cell proliferation through inhibiting cells that are deficient in the enzyme D-amino acid oxidase. It has also been used to inhibit fibroblast growth while allowing the selective growth of epithelial cells.

Valine

Valine is one kinds of the essential amino acids for human being with the requirement of adult males being 10mg/(kg ? d) (FAO/WHO1973). Being lack of this product can cause neurological disorders, reduction of developmental ability as well as anemia. Valine is one of the 20 amino acids that form protein with its chemical name being 2-amino-3-methyl-butyric acid. It belongs to branched chain amino acids and is one of the eight kinds of essential amino acids and carbohydrate-producing amino acids of human body. It works together with the other two high-concentration amino acids (leucine and isoleucine) to promote the normal growth of body, tissue repair, regulate blood sugar, and provide the energy needed. When participating in intense physical activity, valine can provide extra energy to the muscles for producing glucose in order to prevent of muscle weakness. It also helps remove excess nitrogen (potentially toxic) from the liver, and transport nitrogen to all of the rest parts of the body. Valine is an essential amino acid, which means that the human body itself cannot synthesize themselves so that it must be replenished through dietary sources. Its natural food sources include cereals, dairy products, mushrooms, mushrooms, peanuts, soy protein and meat. D-Valine is also found in some actinomyces (such as valeriana). While most people can get sufficient quantities of D-valine from the diet, however, there are still many cases about valine deficiency. Upon being lack of sufficient valine, rats get limb tremors due to disorder of the central nervous system as well as ataxia. Through dissecting slices of brain tissue, it was found about the phenomenon of the red nucleus cell degeneration. Owing to the liver function damage of patients with advanced cirrhosis of the liver, hyperinsulinemia is easy to occur, resulting in the reduction of branched chain amino acids in the blood. The ratio of branched-chain amino acids over aromatic amino acids decreases from 3.0-3.5 (normal body) to 1.0-1.5. It is common for using injection of branched chain amino acids such as valine in the treatment of liver failure, and the damage of alcoholism and drug abuse on these organs.

Uses

Different sources of media describe the Uses of 640-68-6 differently. You can refer to the following data:
1. 1. D-valine can be used for the synthesis of newly efficient pesticide: pyrethroids permethrin and chlorofluorocarbons amyl because of its own biochemical characteristics. The produced valine insecticide permethrin is a broad-spectrum and promising insecticide acaricide which can have effects of touch-killing and stomach poisoning through inhibiting the activity of related enzyme systems of insects. In this way, it can be used for effectively controlling of major pests including Lepidoptera and Diptera in corps such as cotton, fruit trees, and vegetables. D-valine is also widely used in biomedical research. For example, it can be used to inhibit the growth of fibroblasts, and be applied to the studies on its influence on the morphology and function of pulmonary artery endothelial cells. D-valine are also important raw materials as chiral drugs for example it may be used for the synthesis of antineoplastic drugs, anti-diabetes and its complications drugs. With the expansion of the applications fields as well as market demanding of D-valine, the preparation of D-valine will become a hot research field on amino acid. 2. D-Valine is an important organic chiral source which is mainly used in fields such as chiral pharmaceuticals, chiral additive, and chiral auxiliary and other areas. It can also be used as the chiral source of chiral synthesis in the pharmaceutical industry. As an optically active organic acid, it plays an irreplaceable role in the asymmetric synthesis of certain chiral compounds. It is currently mainly used for the production of new broad-spectrum antibiotic, D-valinol, and valine protective agent during the process of peptide synthesis. 3. D-valine is the intermediates for fluvalinate. 4. It is used as a pharmaceutical raw materials and pharmaceutical intermediates, and can also be used for synthetic sweeteners Alatan. 5. It can also be used for biochemical research. The above information is edited by the lookchem of Dai Xiongfeng.
2. D-Valine is an isomer of the essential amino acid L-Valine. D-Valine has been used as a selective agent in epithelial cells in culture since it inhibits cells that lack the enzyme D-amino acid oxidase . D-Valine has also been shown to inhibit proliferation of contaminating fibroblasts in smooth muscle cells from human myometrium. D-Valine solution showed tumor growth inhibition and improvements of the nutritional status in AH109A hepatoma-bearing rats.
3. D-Valine is an isomer of the essential amino acid L-Valine. D-Valine has been used as a selective agent in epithelial cells in culture since it inhibits cells that lack the enzyme D-amino acid oxidase. D-Valine has also been shown to inhibit proliferation of contaminating fibroblasts in smooth muscle cells from human myometrium. D-Valine solution showed tumor growth inhibition and improvements of the nutritional status in AH109A hepatoma-bearing rats.

Chemical Properties

Different sources of media describe the Chemical Properties of 640-68-6 differently. You can refer to the following data:
1. White crystal, m.p.> 295 °C (sublimation), [α] 25 = 27.35°; it is soluble in water and very slightly soluble in ethanol.
2. white to off-white crystalline powder

Production methods

1. DL-Acetyl-methionine is used as the raw material. It undergoes acylase splitting, and further hydrochloric acid acidification to have D-valine crystals precipitated; refined product is finally obtained through recrystallization. 2. The preparation method is to use 2-isopropyl-acetyl ethyl to react with benzene diazonium to get corresponding hydrazine compound, and then further reduce it to valine in zinc-ethanol solution and finally go through chemical or biological split.

References

http://www.sigmaaldrich.com/catalog/product/sigma/v1255?lang=en®ion=US Gilbert, S. F., and B. R. Migeon. "D-valine as a selective agent for normal human and rodent epithelial cells in culture." Cell 5.1(1975):11. Hongpaisan, J. "Inhibition of proliferation of contaminating fibroblasts by D-valine in cultures of smooth muscle cells from human myometrium. " Cell Biology International 24.1(2000):1.

Definition

ChEBI: The D-enantiomer of valine.

General Description

L-Valine is an essential non-polar amino acid. D-Valine is the non-proteinogenic isomer of valine.

Biochem/physiol Actions

D-valine is used in cell culture as a selective inhibitor of cell proliferation, wherein it inhibits cells that lack the enzyme D-amino acid oxidase. Historically D-valine has been used to inhibit fibroblast growth while allowing selective growth of epithelial cells.

Check Digit Verification of cas no

The CAS Registry Mumber 640-68-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,4 and 0 respectively; the second part has 2 digits, 6 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 640-68:
(5*6)+(4*4)+(3*0)+(2*6)+(1*8)=66
66 % 10 = 6
So 640-68-6 is a valid CAS Registry Number.
InChI:InChI=1/C5H11NO2/c1-3(2)4(6)5(7)8/h3-4H,6H2,1-2H3,(H,7,8)/t4-/m1/s1

640-68-6 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (V0012)  D-Valine  >98.0%(T)

  • 640-68-6

  • 1g

  • 120.00CNY

  • Detail
  • TCI America

  • (V0012)  D-Valine  >98.0%(T)

  • 640-68-6

  • 25g

  • 595.00CNY

  • Detail
  • Alfa Aesar

  • (A18894)  D-Valine, 98+%   

  • 640-68-6

  • 5g

  • 256.0CNY

  • Detail
  • Alfa Aesar

  • (A18894)  D-Valine, 98+%   

  • 640-68-6

  • 25g

  • 857.0CNY

  • Detail
  • Alfa Aesar

  • (A18894)  D-Valine, 98+%   

  • 640-68-6

  • 100g

  • 2901.0CNY

  • Detail
  • Sigma

  • (V1255)    suitable for cell culture, BioReagent

  • 640-68-6

  • V1255-1G

  • 210.60CNY

  • Detail
  • Sigma

  • (V1255)    suitable for cell culture, BioReagent

  • 640-68-6

  • V1255-5G

  • 764.01CNY

  • Detail
  • Sigma

  • (V1255)    suitable for cell culture, BioReagent

  • 640-68-6

  • V1255-25G

  • 2,724.93CNY

  • Detail
  • Vetec

  • (V900436)  D-Valine  Vetec reagent grade, 98%

  • 640-68-6

  • V900436-25G

  • 190.71CNY

  • Detail
  • Aldrich

  • (855987)  D-Valine  ≥98%

  • 640-68-6

  • 855987-5G

  • 307.71CNY

  • Detail
  • Aldrich

  • (855987)  D-Valine  ≥98%

  • 640-68-6

  • 855987-25G

  • 1,036.62CNY

  • Detail

640-68-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name D-valine

1.2 Other means of identification

Product number -
Other names H-D-Val-OH

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:640-68-6 SDS

640-68-6Synthetic route

(R)-2-azido-3-methylbutanoic acid
40224-49-5

(R)-2-azido-3-methylbutanoic acid

D-Val-OH
640-68-6

D-Val-OH

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In water; acetic acid under 760 Torr; for 3h;99%
3,3-dimethyl-D-cysteine
52-67-5

3,3-dimethyl-D-cysteine

D-Val-OH
640-68-6

D-Val-OH

Conditions
ConditionsYield
With [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; triethyl phosphite In aq. phosphate buffer; acetonitrile at 20℃; for 0.5h; pH=6.5; Irradiation;96%
tert-butyl 2-amino-3-methylbutanoate
6070-59-3

tert-butyl 2-amino-3-methylbutanoate

D-Val-OH
640-68-6

D-Val-OH

Conditions
ConditionsYield
95%
[3aS-[1(S*),3aα,6α,7aβ]]-1-[(2-amino-3-methyl-1-oxo)butyl]hexahydro-8,8-dimethyl-3H-3a,6-methano-2,1-benzisothiazole-2,2-dioxide monohydrochloride

[3aS-[1(S*),3aα,6α,7aβ]]-1-[(2-amino-3-methyl-1-oxo)butyl]hexahydro-8,8-dimethyl-3H-3a,6-methano-2,1-benzisothiazole-2,2-dioxide monohydrochloride

D-Val-OH
640-68-6

D-Val-OH

Conditions
ConditionsYield
With lithium hydroxide In tetrahydrofuran at 20℃; for 3h; Hydrolysis;88%
(R)-N-benzylvaline
98575-68-9

(R)-N-benzylvaline

D-Val-OH
640-68-6

D-Val-OH

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In acetic acid for 24h;83%
4-<(2R,5S)-2,5-Dihydro-2-isopropyl-3,6-dimethoxy-5-pyrazinyl>butylamine
129243-87-4

4-<(2R,5S)-2,5-Dihydro-2-isopropyl-3,6-dimethoxy-5-pyrazinyl>butylamine

A

D-Val-OH
640-68-6

D-Val-OH

B

L-Lysine hydrochloride
657-27-2, 10098-89-2

L-Lysine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride at 70℃;A n/a
B 80%
With hydrogenchloride at 70℃;
(R)-5-isopropyl-2,2,3-trimethylimidazolidin-4-one

(R)-5-isopropyl-2,2,3-trimethylimidazolidin-4-one

D-Val-OH
640-68-6

D-Val-OH

Conditions
ConditionsYield
With hydrogenchloride; acetic acid In water; toluene at 105℃; for 42h;64%
(R)-3-Methyl-2-(2-oxo-4-phenyl-oxazolidin-3-yl)-butyric acid

(R)-3-Methyl-2-(2-oxo-4-phenyl-oxazolidin-3-yl)-butyric acid

D-Val-OH
640-68-6

D-Val-OH

Conditions
ConditionsYield
With ammonia; lithium In tetrahydrofuran; tert-butyl alcohol at -78℃; for 0.5h;62%
(R)-3-Methyl-2-((R)-2-oxo-4-phenyl-oxazolidin-3-yl)-butyric acid
206068-46-4

(R)-3-Methyl-2-((R)-2-oxo-4-phenyl-oxazolidin-3-yl)-butyric acid

D-Val-OH
640-68-6

D-Val-OH

Conditions
ConditionsYield
With ammonia; lithium In tetrahydrofuran; tert-butyl alcohol at -78℃; for 0.5h; Birch reduction;62%
3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

D-Val-OH
640-68-6

D-Val-OH

Conditions
ConditionsYield
With D-Alanine; meso-diaminopimelate dehydrogenase; pyridoxal 5'-phosphate; alcohol dehydrogenases from Bacillus stearothermophilus; alcohol dehydrogenases from Thermoanaerobacter brockii; NADH In isopropyl alcohol at 35℃; for 9h; pH=8; Reagent/catalyst; Enzymatic reaction; enantioselective reaction;55.6%
With D-glucose; Bacillus subtilis glucose dehydrogenase; Symbiobacterium thermophilum meso-Diaminopimelate dehydrogenase W121L/H227I mutant; NADP; ammonium chloride In aq. buffer at 37℃; for 24h; pH=8.5; Kinetics; Reagent/catalyst; Enzymatic reaction;52%
With D-amino acid transaminase; D-Alanine; R-selective ω-transaminase from Arthrobacter sp; (3-hydroxy-5-hydroxymethyl)-2-methylisonicotinic acid 5-phosphate; isopropylamine In aq. phosphate buffer for 7h; pH=7;n/a
With D-Glucose; Bacillus megaterium glucose dehydrogenase; ammonia; Symbiobacterium thermophilum mesodiaminopimelate dehydrogenase Enzymatic reaction;n/a
3,3-dimethyl-D-cysteine
52-67-5

3,3-dimethyl-D-cysteine

A

D-Val-OH
640-68-6

D-Val-OH

B

L-valine
72-18-4

L-valine

Conditions
ConditionsYield
nickel In water for 1h; Product distribution; Ambient temperature; further amounts of catalyst;A 45%
B n/a
(-)-1-<(1-cyano-2-methylpropyl)amino>-2R-methyl-5R-(1-methylethenyl)-cyclohexane-1R,3R-dicarbonitrile
155385-84-5

(-)-1-<(1-cyano-2-methylpropyl)amino>-2R-methyl-5R-(1-methylethenyl)-cyclohexane-1R,3R-dicarbonitrile

D-Val-OH
640-68-6

D-Val-OH

Conditions
ConditionsYield
With hydrogenchloride at 110℃; for 12h;23%
N-((1R)-1-{[(2,2-dimethoxyethyl)amino]carbonyl}-2-methylpropyl)-N-[(1S)-1-phenylethyl]benzamide

N-((1R)-1-{[(2,2-dimethoxyethyl)amino]carbonyl}-2-methylpropyl)-N-[(1S)-1-phenylethyl]benzamide

D-Val-OH
640-68-6

D-Val-OH

Conditions
ConditionsYield
With hydrogenchloride for 6h; Heating;11%
D,L-valine
516-06-3

D,L-valine

D-Val-OH
640-68-6

D-Val-OH

Conditions
ConditionsYield
durch Vergaerung mit Hefe unter Zusatz von Zucker;
mit Hilfe eines Enzym-Praeparats aus Crotalus adamanteus;
crystallization with L-Phe (1:2 ratio) from water-ethanol (pH 5-6) at 0 deg C;
Conditions
ConditionsYield
With brucine anschliessend Hydrolyse des erhaltenen Formyl-l-valins mit 10prozentiger Bromwasserstoffsaeure;
N-chloroacetyl-D-valine
53518-63-1

N-chloroacetyl-D-valine

D-Val-OH
640-68-6

D-Val-OH

Conditions
ConditionsYield
With hydrogenchloride Hydrolysis;
In water at 37℃; for 0.166667h; Rate constant; D-aminocyclase from Alcaligenes denitrificans DA181, pH 7.8, bovine serum albumin;
2-iodo-propane
75-30-9

2-iodo-propane

Glycine tert-butyl ester
6456-74-2

Glycine tert-butyl ester

A

D-Val-OH
640-68-6

D-Val-OH

B

L-valine
72-18-4

L-valine

Conditions
ConditionsYield
Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;
(R)-2-Amino-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-methyl-butan-1-one

(R)-2-Amino-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-methyl-butan-1-one

D-Val-OH
640-68-6

D-Val-OH

Conditions
ConditionsYield
With lithium hydroxide; ion exchange 1.) THF; Yield given. Multistep reaction;
(3R,6R)-2,5-diethoxy-6-isopropyl-3-<1'-13C>-carboxymethyl-3-methyl-6-hydropyrazine
133444-95-8

(3R,6R)-2,5-diethoxy-6-isopropyl-3-<1'-13C>-carboxymethyl-3-methyl-6-hydropyrazine

A

D-Val-OH
640-68-6

D-Val-OH

B

(2R)-<1-13C>-2-amino-2-methylmalonic acid
129145-03-5

(2R)-<1-13C>-2-amino-2-methylmalonic acid

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide 1) CH3CN, RT, 18h, 2) 70 deg C, 15 min; Multistep reaction;
δ-(L-α-aminoadipoyl)-L-serine-D-valine
74784-08-0, 133444-29-8

δ-(L-α-aminoadipoyl)-L-serine-D-valine

A

D-Val-OH
640-68-6

D-Val-OH

B

L-serin
56-45-1

L-serin

C

L-homoglutamic acid
1118-90-7

L-homoglutamic acid

Conditions
ConditionsYield
With hydrogenchloride at 110℃; for 21h; Product distribution;
(R)-3-Methyl-2-((S)-1-phenyl-ethylamino)-butyric acid
42454-74-0

(R)-3-Methyl-2-((S)-1-phenyl-ethylamino)-butyric acid

D-Val-OH
640-68-6

D-Val-OH

Conditions
ConditionsYield
With palladium hydroxide - carbon for 24h; Yield given;
D,L-valine
516-06-3

D,L-valine

(S)-2-{(N-benzyl-2-pyrrolidinyl)carbonylamino}benzaldehyde
82704-14-1

(S)-2-{(N-benzyl-2-pyrrolidinyl)carbonylamino}benzaldehyde

A

D-Val-OH
640-68-6

D-Val-OH

B

L-valine
72-18-4

L-valine

Conditions
ConditionsYield
With hydrogenchloride; sodium methylate; nickel(II) nitrate Product distribution; 1.) MeOH, 40 deg C, 24 h, 2.) reflux;
D,L-valine
516-06-3

D,L-valine

A

D-Val-OH
640-68-6

D-Val-OH

B

L-valine
72-18-4

L-valine

Conditions
ConditionsYield
resolution of underivatized amino acids enantiomers by liquid chromatography using a chiral eluant Cu(L-Pro)2 and a reversed-phase column; other chiral eluants, pH dependence;
(2S,5S)-N-<(S)-N-bis(methylthio)methylenevalyl>-2,5-bis(methoxymethoxymethyl)pyrrolidine
108437-93-0

(2S,5S)-N-<(S)-N-bis(methylthio)methylenevalyl>-2,5-bis(methoxymethoxymethyl)pyrrolidine

A

D-Val-OH
640-68-6

D-Val-OH

B

L-valine
72-18-4

L-valine

Conditions
ConditionsYield
With hydrogenchloride for 4h; Heating; Yield given;
(R)-2-[((R)-Carboxy-phenyl-methyl)-amino]-3-methyl-butyric acid
112496-42-1

(R)-2-[((R)-Carboxy-phenyl-methyl)-amino]-3-methyl-butyric acid

D-Val-OH
640-68-6

D-Val-OH

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal
(S)-2-<(R)-2-hydroxy-1-phenylethylamino>-3-methylbutanoic acid
145058-01-1

(S)-2-<(R)-2-hydroxy-1-phenylethylamino>-3-methylbutanoic acid

A

D-Val-OH
640-68-6

D-Val-OH

B

L-valine
72-18-4

L-valine

Conditions
ConditionsYield
With formic acid In methanol; water Ambient temperature; Yield given. Yields of byproduct given;
(2R,2'R)-N-(2'-amino-3'-methylbutanoyl)bornane-10,2-sultam hydrochloride
129568-82-7

(2R,2'R)-N-(2'-amino-3'-methylbutanoyl)bornane-10,2-sultam hydrochloride

D-Val-OH
640-68-6

D-Val-OH

Conditions
ConditionsYield
With lithium hydroxide; Amberlite IR-120 1) THF, room temperature, 2) H2O, room temperature, 15 h; Yield given. Multistep reaction;
(3S,6R)-2,5-dimethoxy-3-((2'R)-methoxypropionyl)-6-isopropyl-3,6-dihydropyrazine

(3S,6R)-2,5-dimethoxy-3-((2'R)-methoxypropionyl)-6-isopropyl-3,6-dihydropyrazine

A

D-Val-OH
640-68-6

D-Val-OH

B

(2S,3S)-3-methylaspartic acid
6061-13-8

(2S,3S)-3-methylaspartic acid

C

erythro-β-methyl-L-aspartate
7298-96-6

erythro-β-methyl-L-aspartate

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide 1.) acetonitrile, RT, 12 h, 2.) acetonitrile, 70 deg C, 15 min; Yield given. Multistep reaction. Title compound not separated from byproducts;
glycine
56-40-6

glycine

isopropyl bromide
75-26-3

isopropyl bromide

A

D-Val-OH
640-68-6

D-Val-OH

B

L-valine
72-18-4

L-valine

Conditions
ConditionsYield
Yield given. Multistep reaction. Yields of byproduct given;
With hydrogenchloride; sodium hydroxide; S-2-N-(N'-benzylprolyl)aminibenzophenone; sodium methylate 1.) methanol, 2.) DMF, 20 deg C, 30 min, 3.) methanol, reflux; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;
ethanol
64-17-5

ethanol

D-Val-OH
640-68-6

D-Val-OH

(R)-(-)-valine ethyl ester hydrochloride

(R)-(-)-valine ethyl ester hydrochloride

Conditions
ConditionsYield
With thionyl chloride for 4h; Heating;100%
With thionyl chloride
With thionyl chloride at 20℃;
nicotinic acid
59-67-6

nicotinic acid

D-Val-OH
640-68-6

D-Val-OH

(R)-1-carboxy-2-methylpropan-1-aminium nicotinate

(R)-1-carboxy-2-methylpropan-1-aminium nicotinate

Conditions
ConditionsYield
In water for 0.166667h; pH=Ca. 3.3 - 3.9; Cooling with ice;100%
D-Val-OH
640-68-6

D-Val-OH

benzaldehyde
100-52-7

benzaldehyde

C12H15NO2

C12H15NO2

Conditions
ConditionsYield
In toluene for 4h; Reflux;99.8%
D-Val-OH
640-68-6

D-Val-OH

(R)-2-Hydroxy-3-methylbutyric acid
17407-56-6

(R)-2-Hydroxy-3-methylbutyric acid

Conditions
ConditionsYield
With sulfuric acid; water; sodium nitrite at 60℃; Flow reactor;99%
With sulfuric acid; sodium nitrite In water at 60℃; under 5171.62 Torr; Inert atmosphere;80%
With sulfuric acid; sodium nitrite In water at 0 - 20℃; for 12h;65%
D-Val-OH
640-68-6

D-Val-OH

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

Boc-D-Val-OH
22838-58-0

Boc-D-Val-OH

Conditions
ConditionsYield
With sodium hydrogencarbonate In tetrahydrofuran; water for 16h; Reflux;99%
With sodium hydrogencarbonate In water94%
With sodium hydroxide In tetrahydrofuran; water for 2h;92%
D-Val-OH
640-68-6

D-Val-OH

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

D-valine N-carboxy anhydride
43089-05-0

D-valine N-carboxy anhydride

Conditions
ConditionsYield
In tetrahydrofuran at 45 - 50℃;99%
D-Val-OH
640-68-6

D-Val-OH

3-chloro-4-fluoro benzotrifluoride
78068-85-6

3-chloro-4-fluoro benzotrifluoride

2-(2-chloro-α,α,α-trifluoro-p-toluidino)-3-methylbutyric acid
76338-73-3

2-(2-chloro-α,α,α-trifluoro-p-toluidino)-3-methylbutyric acid

Conditions
ConditionsYield
With potassium carbonate99%
D-Val-OH
640-68-6

D-Val-OH

3-carbamoyl-1-(2,4-dinitrophenyl)pyridinium chloride
53406-00-1

3-carbamoyl-1-(2,4-dinitrophenyl)pyridinium chloride

C11H15N2O3(1+)

C11H15N2O3(1+)

Conditions
ConditionsYield
With triethylamine In methanol at 20℃; for 24h;98.5%
methanol
67-56-1

methanol

D-Val-OH
640-68-6

D-Val-OH

D-Valine methyl ester hydrochloride
7146-15-8

D-Valine methyl ester hydrochloride

Conditions
ConditionsYield
With thionyl chloride 1.) -15 deg C, 40 min, 2.) 40 deg C, 2 h;98%
With thionyl chloride at 20℃;96%
With thionyl chloride at 20℃; Inert atmosphere;94%
n-dodecanoyl chloride
112-16-3

n-dodecanoyl chloride

D-Val-OH
640-68-6

D-Val-OH

N-lauroyl-D-valine
14379-29-4

N-lauroyl-D-valine

Conditions
ConditionsYield
Stage #1: D-Val-OH With pyridine; chloro-trimethyl-silane In dichloromethane for 1.16667h;
Stage #2: n-dodecanoyl chloride In dichloromethane at 0 - 20℃; for 1.83333h; Enzymatic reaction;
98%
Stage #1: n-dodecanoyl chloride; D-Val-OH With sodium hydroxide In water; acetone at 0 - 5℃;
Stage #2: With hydrogenchloride In water; acetone pH=1;
D-Val-OH
640-68-6

D-Val-OH

Λ-[Ir(2-phenylquinoline)2(MeCN)2](PF6)

Λ-[Ir(2-phenylquinoline)2(MeCN)2](PF6)

Δ-[Ir(pq)2(D-val)]

Δ-[Ir(pq)2(D-val)]

Conditions
ConditionsYield
With sodium methylate In methanol at 20℃; for 12h; Darkness;98%
D-Val-OH
640-68-6

D-Val-OH

2,2,2-trifluoroethyl chloroformate
27746-99-2

2,2,2-trifluoroethyl chloroformate

N-(2,2,2-trifluoroethoxycarbonyl)-D-valine

N-(2,2,2-trifluoroethoxycarbonyl)-D-valine

Conditions
ConditionsYield
With sodium hydroxide In water; toluene at 5 - 10℃; for 1h; pH=12;97.3%
D-Val-OH
640-68-6

D-Val-OH

(1S,3E)-5-<(2,5-dioxo-1-pyrrolidinyl)oxy>-1-<(1R,2E)-1-methyl-3-phenyl-2-propenyl>-5-oxo-3-pentenyl-(2S)-<3-<<(1,1-dimethylethoxy)carbonyl>amino>-2,2-dimethyl-1-oxopropoxy>-4-methylpentanoate
188346-51-2

(1S,3E)-5-<(2,5-dioxo-1-pyrrolidinyl)oxy>-1-<(1R,2E)-1-methyl-3-phenyl-2-propenyl>-5-oxo-3-pentenyl-(2S)-<3-<<(1,1-dimethylethoxy)carbonyl>amino>-2,2-dimethyl-1-oxopropoxy>-4-methylpentanoate

N-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-(methylpentanoyl)-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoyl-D-valine
240428-49-3

N-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-(methylpentanoyl)-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoyl-D-valine

Conditions
ConditionsYield
With N,O-bis-(trimethylsilyl)-acetamide In N,N-dimethyl-formamide at 55 - 60℃;96%
formaldehyd
50-00-0

formaldehyd

D-Val-OH
640-68-6

D-Val-OH

(R)-2-(N,N-dimethylamino)-3-methylbutanoic acid
899900-52-8

(R)-2-(N,N-dimethylamino)-3-methylbutanoic acid

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In water at 20℃; under 760.051 Torr; for 120h;96%
With hydrogen; palladium on activated charcoal In water at 20℃;
With 5%-palladium/activated carbon; hydrogen In water at 20℃; for 120h;
With sodium cyanoborohydride In water for 0.5h; Cooling with ice;
D-Val-OH
640-68-6

D-Val-OH

(fluorenylmethoxy)carbonyl chloride
28920-43-6

(fluorenylmethoxy)carbonyl chloride

N-(9-fluorenylmethoxycarbonyl)-D-valine
84624-17-9

N-(9-fluorenylmethoxycarbonyl)-D-valine

Conditions
ConditionsYield
With sodium carbonate In 1,4-dioxane at 0 - 20℃;96%
With sodium carbonate In 1,4-dioxane; water at 0 - 20℃; for 1h; Inert atmosphere;
D-Val-OH
640-68-6

D-Val-OH

isopropyl alcohol
67-63-0

isopropyl alcohol

Val-O-iPr+ (Cl-)

Val-O-iPr+ (Cl-)

Conditions
ConditionsYield
With thionyl chloride at 0℃; Reflux;95%
With hydrogenchloride
With hydrogenchloride
[Pd(2-phenylpyridine-C(2),N')(μ-Cl)]2
135681-05-9, 20832-86-4

[Pd(2-phenylpyridine-C(2),N')(μ-Cl)]2

D-Val-OH
640-68-6

D-Val-OH

Pd(NC5H4C6H4)(NH2CH(CH(CH3)2)CO2)

Pd(NC5H4C6H4)(NH2CH(CH(CH3)2)CO2)

Conditions
ConditionsYield
With NaOMe In methanol N2-atmosphere; dropwise addn. of 1 equiv. NaOMe to aminoacid, gentle heating to dissoln., addn. of stoich. amt. Pd-complex, stirring for 14-18 h; centrifugation, solvent removal (vac.), extn. into DMF, solvent removal (vac.), washing (water), drying (vac., 60°C, 9 h); elem. anal.;95%
D-Val-OH
640-68-6

D-Val-OH

benzyl chloroformate
501-53-1

benzyl chloroformate

Z-D-proline
6404-31-5

Z-D-proline

Conditions
ConditionsYield
With sodium hydroxide at 0℃;95%
dichlorotricarbonylruthenium(II) dimer

dichlorotricarbonylruthenium(II) dimer

D-Val-OH
640-68-6

D-Val-OH

Ru(CO)3Cl-D-valinate

Ru(CO)3Cl-D-valinate

Conditions
ConditionsYield
With sodium methylate In methanol at 20℃; for 24h; Inert atmosphere;94.8%
formaldehyd
50-00-0

formaldehyd

D-Val-OH
640-68-6

D-Val-OH

butane-2,3-dione mono-oxime
135636-66-7

butane-2,3-dione mono-oxime

(R)-2-(4,5-Dimethyl-3-oxy-imidazol-1-yl)-3-methyl-butyric acid
122459-37-4

(R)-2-(4,5-Dimethyl-3-oxy-imidazol-1-yl)-3-methyl-butyric acid

Conditions
ConditionsYield
In ethanol for 3h; Heating;94%
bromochlorobenzene
106-39-8

bromochlorobenzene

D-Val-OH
640-68-6

D-Val-OH

(4-chlorophenyl)-D-valine

(4-chlorophenyl)-D-valine

Conditions
ConditionsYield
With D-myo-inositol; copper; caesium carbonate In water at 100℃; for 10h;94%
D-Val-OH
640-68-6

D-Val-OH

benzyl chloroformate
501-53-1

benzyl chloroformate

N-[(benzyloxy)carbonyl]-D-valine
1685-33-2

N-[(benzyloxy)carbonyl]-D-valine

Conditions
ConditionsYield
With sodium hydrogencarbonate Acylation;93%
With sodium hydrogencarbonate at 0 - 20℃;93%
With sodium hydrogencarbonate at 0 - 20℃;93%
D-Val-OH
640-68-6

D-Val-OH

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

D-valine N-carboxy anhydride
43089-05-0

D-valine N-carboxy anhydride

Conditions
ConditionsYield
With pyrographite In tetrahydrofuran at 60℃; for 1h;93%
methanol
67-56-1

methanol

D-Val-OH
640-68-6

D-Val-OH

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

Toluene-4-sulfonic acid; compound with (R)-2-amino-3-methyl-butyric acid methyl ester

Toluene-4-sulfonic acid; compound with (R)-2-amino-3-methyl-butyric acid methyl ester

Conditions
ConditionsYield
With p-toluenesulfonyl chloride for 20h; Heating;93%
phthalic anhydride
85-44-9

phthalic anhydride

D-Val-OH
640-68-6

D-Val-OH

Conditions
ConditionsYield
With triethylamine In toluene Heating;92%
at 150℃;
With triethylamine In toluene Reflux; Inert atmosphere;
D-Val-OH
640-68-6

D-Val-OH

(R)-2-amino-3-methylbutanol
4276-09-9

(R)-2-amino-3-methylbutanol

Conditions
ConditionsYield
With lithium borohydride; chloro-trimethyl-silane In tetrahydrofuran at 20℃; for 0.25h; Reduction;92%
With sodium tetrahydroborate; iodine In tetrahydrofuran Inert atmosphere;91%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 17h; Reflux;74%
D-Val-OH
640-68-6

D-Val-OH

isobutyraldehyde
78-84-2

isobutyraldehyde

butane-2,3-dione mono-oxime
135636-66-7

butane-2,3-dione mono-oxime

1-α-Carboxyisobutyl-2-isopropyl-4,5-dimethylimidazol-3-oxid
133286-87-0

1-α-Carboxyisobutyl-2-isopropyl-4,5-dimethylimidazol-3-oxid

Conditions
ConditionsYield
In acetic acid for 1h; Heating;92%

640-68-6Relevant articles and documents

Polyketides, diketopiperazines and an isochromanone from the marine-derived fungal strain Fusarium graminearum FM1010 from Hawaii

Cao, Shugeng,Sarotti, Ariel M.,Uz Zaman, KH Ahammad,Wu, Xiaohua

, (2022/03/09)

The fungal strain Fusarium graminearum FM1010 was isolated from a shallow-water volcanic rock known as “live rock” at the Carl Smith Beach, Hilo, Hawaii. Eleven specialised metabolites, including two undescribed diketopiperazines, three undescribed polyketides, and one undescribed isochromanone, along with five known fusarielin derivatives were obtained from F. graminearum FM1010. The structures of the six undescribed compounds were elucidated by extensive analysis of NMR spectroscopy, HRESIMS, chemical reactions, and electronic circular dichroism (ECD) data. Kaneoheoic acids G-I showed mild inhibitory activity against S. aureus with the MIC values in the range of 20–40 μg/mL when assayed in combination with chloramphenicol (half of the MIC, 1 μg/mL), an FDA approved antibiotic. Kaneoheoic acid I exhibited both anti-proliferative activity against ovarian cancer cell line A2780 and TNF-α induced NF-κB inhibitory activity with the IC50 values of 18.52 and 15.86 μM, respectively.

Simultaneous Preparation of (S)-2-Aminobutane and d -Alanine or d -Homoalanine via Biocatalytic Transamination at High Substrate Concentration

Li, Jianjiong,Wang, Yingang,Wu, Qiaqing,Yao, Peiyuan,Yu, Shanshan,Zhu, Dunming

supporting information, (2022/03/01)

(S)-2-Aminobutane, d-alanine, and d-homoalanine are important intermediates for the production of various active pharmaceutical ingredients and food additives. The preparation of these small chiral amine or amino acids with high water solubility still demands searching for efficient methods. In this work, we identified an ω-transaminase (ω-TA) from Sinirhodobacter hungdaonensis (ShdTA) that catalyzed the kinetic resolution of racemic 2-aminobutane at a concentration of 800 mM using pyruvate as the amino acceptor, leading to the simultaneous isolation of enantiopure (S)-2-aminobutane and d-alanine in 46% and 90% yield, respectively. In addition, (S)-2-aminobutane (98% ee) and d-homoalanine (99% ee) were isolated in 45% and 93% yield, respectively, in the kinetic resolution of racemic 2-aminobutane at a concentration of 400 mM coupled with deamination of l-threonine by threonine deaminase. We thus developed a biocatalytic process for the practical synthesis of these valuable small chiral amine and d-amino acids.

Targeted Isolation of Asperheptatides from a Coral-Derived Fungus Using LC-MS/MS-Based Molecular Networking and Antitubercular Activities of Modified Cinnamate Derivatives

Chao, Rong,Hou, Xue-Mei,Xu, Wei-Feng,Hai, Yang,Wei, Mei-Yan,Wang, Chang-Yun,Gu, Yu-Cheng,Shao, Chang-Lun

, p. 11 - 19 (2021/01/14)

Under the guidance of MS/MS-based molecular networking, four new cycloheptapeptides, namely, asperheptatides A-D (1-4), were isolated together with three known analogues, asperversiamide A-C (5-7), from the coral-derived fungus Aspergillus versicolor. The planar structures of the two major compounds, asperheptatides A and B (1 and 2), were determined by comprehensive spectroscopic data analysis. The absolute configurations of the amino acid residues were determined by advanced Marfey's method. The two structurally related trace metabolites, asperheptatides C and D (3 and 4), were characterized by ESI-MS/MS fragmentation methods. A series of new derivatives (8-26) of asperversiamide A (5) were semisynthesized. The antitubercular activities of 1, 2, and 5-26 against Mycobacterium tuberculosis H37Ra were also evaluated. Compounds 9, 13, 23, and 24 showed moderate activities with MIC values of 12.5 μM, representing a potential new class of antitubercular agents.

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