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319-78-8 Usage

Chemical Properties

white to very slightly yellow powder

Uses

Different sources of media describe the Uses of 319-78-8 differently. You can refer to the following data:
1. May contain up to 10% allo-isomer.
2. D-Isoleucine is not biosynthesized in the human body and is therefore categorized as an essential amino acid that must be obtained through diet. It is also an important building block that is used in the formation of hemoglobin in humans.

Definition

ChEBI: The D-enantiomer of isoleucine.

Check Digit Verification of cas no

The CAS Registry Mumber 319-78-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,1 and 9 respectively; the second part has 2 digits, 7 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 319-78:
(5*3)+(4*1)+(3*9)+(2*7)+(1*8)=68
68 % 10 = 8
So 319-78-8 is a valid CAS Registry Number.
InChI:InChI=1/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)

319-78-8 Well-known Company Product Price

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  • Alfa Aesar

  • (H27488)  D-Isoleucine, 98%   

  • 319-78-8

  • 250mg

  • 2774.0CNY

  • Detail
  • Alfa Aesar

  • (H27488)  D-Isoleucine, 98%   

  • 319-78-8

  • 1g

  • 7324.0CNY

  • Detail

319-78-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name D-isoleucine

1.2 Other means of identification

Product number -
Other names D-Isoleucine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
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:319-78-8 SDS

319-78-8Synthetic route

Conditions
ConditionsYield
With C13H15NO5V(1-)*C16H36N(1+) In ethanol; waterA 32%
B n/a
With C13H15NO5V(1-)*C16H36N(1+) In ethanol; waterA n/a
B 22%
Conditions
ConditionsYield
durch Einw. von gaerender Hefe;
crystallization with L-Phe (1:2 ratio) from water-ethanol (pH 5-6) at 25 deg C;
Multi-step reaction with 2 steps
2: brucine / man zerlegt in die optisch aktiven Komponenten und erwaermt mit 10prozentiger Salzsaeure auf dem Wasserbad
View Scheme
(-)(2S:3R)-2-bromo-3-methyl-valeric acid
21582-41-2

(-)(2S:3R)-2-bromo-3-methyl-valeric acid

D-Isoleucine
319-78-8

D-Isoleucine

Conditions
ConditionsYield
bei Ueberfuehrung in das (Carboxymetyl)-amid, folgender Aminierung und Hydrolyse;
N-formyl-isoleucine
4101-35-3, 89810-44-6

N-formyl-isoleucine

D-Isoleucine
319-78-8

D-Isoleucine

Conditions
ConditionsYield
With brucine man zerlegt in die optisch aktiven Komponenten und erwaermt mit 10prozentiger Salzsaeure auf dem Wasserbad;
With brucine man zerlegt in die optisch aktiven Komponenten und erwaermt mit 20prozentiger Bromwasserstoffsaeure;
N-formyl-D-isoleucine
907582-55-2

N-formyl-D-isoleucine

D-Isoleucine
319-78-8

D-Isoleucine

Conditions
ConditionsYield
With hydrogen bromide
(2R,3R)-2-acetamido-3-methylpentanoic acid
19764-31-9

(2R,3R)-2-acetamido-3-methylpentanoic acid

D-Isoleucine
319-78-8

D-Isoleucine

Conditions
ConditionsYield
With hydrogenchloride
With Escherichia coli D-aminoacylase amano In phosphate buffer at 37℃; for 12h; pH=8.0;
Stage #1: (2R,3R)-2-acetamido-3-methylpentanoic acid With hydrogenchloride; water at 80℃;
Stage #2: With triethylamine
N-D-isoleucyl-glycine
868-28-0

N-D-isoleucyl-glycine

A

D-Isoleucine
319-78-8

D-Isoleucine

B

glycine
56-40-6

glycine

Conditions
ConditionsYield
Hydrolysis;
N-chloroacetyl-D-isoleucine
907582-60-9

N-chloroacetyl-D-isoleucine

D-Isoleucine
319-78-8

D-Isoleucine

Conditions
ConditionsYield
With hydrogenchloride
L-isoleucine
73-32-5

L-isoleucine

D-Isoleucine
319-78-8

D-Isoleucine

Conditions
ConditionsYield
With hydrogenchloride; ethanethiol at 110℃; Rate constant; various times;
(S)-1-phenyl-ethylamine
2627-86-3

(S)-1-phenyl-ethylamine

2-methyl-4-sec-butylidene-5-oxazolone

2-methyl-4-sec-butylidene-5-oxazolone

A

D-allo-isoleucine
1509-34-8

D-allo-isoleucine

B

L-isoleucine
73-32-5

L-isoleucine

C

D-Isoleucine
319-78-8

D-Isoleucine

D

D-alloisoleucine
1509-35-9

D-alloisoleucine

Conditions
ConditionsYield
Product distribution; Rate constant; multistep reaction;
(2S,3R)-2-Azido-3-methyl-pentanoic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester
106749-12-6

(2S,3R)-2-Azido-3-methyl-pentanoic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester

A

D-allo-isoleucine
1509-34-8

D-allo-isoleucine

B

L-isoleucine
73-32-5

L-isoleucine

C

D-Isoleucine
319-78-8

D-Isoleucine

D

D-alloisoleucine
1509-35-9

D-alloisoleucine

Conditions
ConditionsYield
With titanium tetrakis(benzyl alkoxide); hydrogen; Pd-BaSO4 1.) benzyl alcohol, 130 gradC 2.) EtOH, EtOAc, 1 atm, r.t.; Yield given. Multistep reaction. Title compound not separated from byproducts;
1-p-chlorophenylsulphonylimino-2,3-dihydro-9-methyl-1H-pyrrolo<1,2-a>indole
76569-26-1

1-p-chlorophenylsulphonylimino-2,3-dihydro-9-methyl-1H-pyrrolo<1,2-a>indole

A

dihydro-5-butyl-5-methyl-2-(3H)-furanone
3285-00-5

dihydro-5-butyl-5-methyl-2-(3H)-furanone

B

5-hexyl-5-methyldihydro-2(3H)-furanone
7011-83-8, 187600-82-4

5-hexyl-5-methyldihydro-2(3H)-furanone

C

D-Isoleucine
319-78-8

D-Isoleucine

D

L-phenylalanine
63-91-2

L-phenylalanine

Conditions
ConditionsYield
With hydrogenchloride; beauverolide Ka; D-amino-acid oxidase; sodium pyrophosphate buffer 1.) 110 deg C, 3 d, 2.) 38 deg C, 1 h; Multistep reaction;
1-p-chlorophenylsulphonylimino-2,3-dihydro-9-methyl-1H-pyrrolo<1,2-a>indole
76569-26-1

1-p-chlorophenylsulphonylimino-2,3-dihydro-9-methyl-1H-pyrrolo<1,2-a>indole

A

D-Isoleucine
319-78-8

D-Isoleucine

B

L-phenylalanine
63-91-2

L-phenylalanine

Conditions
ConditionsYield
With phosphate buffer; beauverolide Ka; D-amino-acidoxidase; toluene-4-sulfonic acid 1.) 110 deg C, 20 h, 2.)38 deg C, 2 h; Multistep reaction;
1-p-chlorophenylsulphonylimino-2,3-dihydro-9-methyl-1H-pyrrolo<1,2-a>indole
76569-26-1

1-p-chlorophenylsulphonylimino-2,3-dihydro-9-methyl-1H-pyrrolo<1,2-a>indole

A

D-Isoleucine
319-78-8

D-Isoleucine

B

L-phenylalanine
63-91-2

L-phenylalanine

C

L-Tryptophan
73-22-3

L-Tryptophan

Conditions
ConditionsYield
With phosphate buffer; beauverolide Ka; D-amino-acidoxidase; toluene-4-sulfonic acid 1.) 110 deg C, 20 h, 2.)38 deg C, 2 h; Multistep reaction;
3-sec-butyl-6-isopropyl-piperazine-2,5-dione
104068-43-1

3-sec-butyl-6-isopropyl-piperazine-2,5-dione

hydrogen bromide
10035-10-6, 12258-64-9

hydrogen bromide

A

D-Val-OH
640-68-6

D-Val-OH

B

D-Isoleucine
319-78-8

D-Isoleucine

Conditions
ConditionsYield
at 115 - 120℃;
active α-bromo-β-methyl-β-ethyl-propionic acid

active α-bromo-β-methyl-β-ethyl-propionic acid

D-Isoleucine
319-78-8

D-Isoleucine

Conditions
ConditionsYield
With ammonia; water at 37℃;
bituminous peat

bituminous peat

A

L-leucine
61-90-5

L-leucine

B

D-Isoleucine
319-78-8

D-Isoleucine

Conditions
ConditionsYield
With sulfuric acid
hydrogen cyanide
74-90-8

hydrogen cyanide

(S)-2-methylbutyraldehyde
1730-97-8

(S)-2-methylbutyraldehyde

ammonia
7664-41-7

ammonia

A

D-Isoleucine
319-78-8

D-Isoleucine

B

D-alloisoleucine
1509-35-9

D-alloisoleucine

Conditions
ConditionsYield
Verseifen des entstandenen Aminovaleronitrils;
N-isoleucyl-glycine
868-28-0

N-isoleucyl-glycine

sulfuric acid (25 percent )

sulfuric acid (25 percent )

A

D-Isoleucine
319-78-8

D-Isoleucine

B

glycine
56-40-6

glycine

Conditions
ConditionsYield
-glycine;
(R)-3-Methyl-pentanoic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester
106749-13-7

(R)-3-Methyl-pentanoic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester

D-Isoleucine
319-78-8

D-Isoleucine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 67 percent / LDA, Me3SiCl, NBS
2: 93 percent / NaN3 / dimethylformamide / 60 h / Ambient temperature
3: 1.) Ti(OCH2Ph)4 2.) H2 / 2.) Pd/BaSO4 / 1.) benzyl alcohol, 130 gradC 2.) EtOH, EtOAc, 1 atm, r.t.
View Scheme
(2R,3R)-2-Bromo-3-methyl-pentanoic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester
106749-11-5

(2R,3R)-2-Bromo-3-methyl-pentanoic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester

D-Isoleucine
319-78-8

D-Isoleucine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 93 percent / NaN3 / dimethylformamide / 60 h / Ambient temperature
2: 1.) Ti(OCH2Ph)4 2.) H2 / 2.) Pd/BaSO4 / 1.) benzyl alcohol, 130 gradC 2.) EtOH, EtOAc, 1 atm, r.t.
View Scheme
Conditions
ConditionsYield
With shaking calcined L-Pro chiral ordered mesoporous silica Resolution of racemate;
With R-(3,3'-dibromo-1,1'-binaphthyl)-20-crown-6 coated C18 silica gel column at 25℃; pH=2; Resolution of racemate;
With capillary electrochromatography open-tubular column coated with 1-allylimidazolium-β-cyclodextrin In aq. acetate buffer at 20℃; pH=8; pH-value; Resolution of racemate;
calyxamide B
1356449-88-1

calyxamide B

A

L-alanin
56-41-7

L-alanin

B

(S)-2,3-diaminopropionic acid
515-94-6, 1915-96-4, 4033-39-0, 6018-54-8

(S)-2,3-diaminopropionic acid

C

L-isoleucine
73-32-5

L-isoleucine

D

D-Isoleucine
319-78-8

D-Isoleucine

E

L-glutamine
56-85-9

L-glutamine

Conditions
ConditionsYield
Stage #1: calyxamide B With dihydrogen peroxide; sodium hydroxide at 65℃; for 0.666667h;
Stage #2: With hydrogenchloride; water at 110℃; for 24h;
cyclo-(-L-Ile-D-Ile-L-Lys-L-Ile-D-Phe-D-Leu-L-Ile-D-Ala-)
1444002-12-3

cyclo-(-L-Ile-D-Ile-L-Lys-L-Ile-D-Phe-D-Leu-L-Ile-D-Ala-)

A

D-Alanine
338-69-2

D-Alanine

B

(R)-leucine
328-38-1

(R)-leucine

C

L-isoleucine
73-32-5

L-isoleucine

D

D-Isoleucine
319-78-8

D-Isoleucine

E

L-lysine
56-87-1

L-lysine

F

D-(R)-phenylalanine
673-06-3

D-(R)-phenylalanine

Conditions
ConditionsYield
With hydrogenchloride In water at 110℃;
surugamides C
1444002-14-5

surugamides C

A

D-Alanine
338-69-2

D-Alanine

B

L-valine
72-18-4

L-valine

C

(R)-leucine
328-38-1

(R)-leucine

D

L-isoleucine
73-32-5

L-isoleucine

E

D-Isoleucine
319-78-8

D-Isoleucine

F

L-lysine
56-87-1

L-lysine

G

D-(R)-phenylalanine
673-06-3

D-(R)-phenylalanine

Conditions
ConditionsYield
With hydrogenchloride In water at 110℃;
surugamides D
1444002-15-6

surugamides D

A

D-Alanine
338-69-2

D-Alanine

B

L-valine
72-18-4

L-valine

C

(R)-leucine
328-38-1

(R)-leucine

D

L-isoleucine
73-32-5

L-isoleucine

E

D-Isoleucine
319-78-8

D-Isoleucine

F

L-lysine
56-87-1

L-lysine

G

D-(R)-phenylalanine
673-06-3

D-(R)-phenylalanine

Conditions
ConditionsYield
With hydrogenchloride In water at 110℃;
surugamides E
1444002-16-7

surugamides E

A

D-Alanine
338-69-2

D-Alanine

B

L-valine
72-18-4

L-valine

C

(R)-leucine
328-38-1

(R)-leucine

D

L-isoleucine
73-32-5

L-isoleucine

E

D-Isoleucine
319-78-8

D-Isoleucine

F

L-lysine
56-87-1

L-lysine

G

D-(R)-phenylalanine
673-06-3

D-(R)-phenylalanine

Conditions
ConditionsYield
With hydrogenchloride In water at 110℃;
D-allo-isoleucine
1509-34-8

D-allo-isoleucine

D-Isoleucine
319-78-8

D-Isoleucine

Conditions
ConditionsYield
With ammonium metavanadate; salicylaldehyde; sodium hydroxide In water for 6h; pH=11; Reflux;
D-Isoleucine
319-78-8

D-Isoleucine

tetrachlorophthalic anhydride
117-08-8

tetrachlorophthalic anhydride

TCP-D-Ile-OH

TCP-D-Ile-OH

Conditions
ConditionsYield
In N,N-dimethyl-formamide Microwave irradiation;98%
D-Isoleucine
319-78-8

D-Isoleucine

ethyl trifluoroacetate,
383-63-1

ethyl trifluoroacetate,

(2R,3R)-3-methyl-2-(2,2,2-trifluoroacetamido)pentanoic acid

(2R,3R)-3-methyl-2-(2,2,2-trifluoroacetamido)pentanoic acid

Conditions
ConditionsYield
With triethylamine In methanol at 20℃; for 24h;96%
D-Isoleucine
319-78-8

D-Isoleucine

2-((tert-butoxycarbonyloxy)imino)-2-phenylacetonitrile

2-((tert-butoxycarbonyloxy)imino)-2-phenylacetonitrile

Boc-D-Ile-OH
55721-65-8

Boc-D-Ile-OH

Conditions
ConditionsYield
With triethylamine In water; acetone for 5h; Ambient temperature;95%
D-Isoleucine
319-78-8

D-Isoleucine

(2R,3R)-2-bromo-3-methylpentanoic acid
94318-70-4

(2R,3R)-2-bromo-3-methylpentanoic acid

Conditions
ConditionsYield
With hydrogen bromide; sodium nitrite In water at 0 - 20℃; for 16h;95%
With hydrogen bromide; potassium bromide; sodium nitrite Substitution;
With hydrogen bromide; sodium nitrite In water at 0 - 20℃; for 16h;
D-Isoleucine
319-78-8

D-Isoleucine

Conditions
ConditionsYield
With sulfuric acid; sodium nitrite93%
Stage #1: D-Isoleucine With sodium nitrite In water
Stage #2: With sulfuric acid; water
85%
With hydrogenchloride; acetic acid; sodium nitrite
D-Isoleucine
319-78-8

D-Isoleucine

3-(N-benzyloxycarbonyl-L-leucyl)-1,3-thiazolidine-2-thione
78569-22-9

3-(N-benzyloxycarbonyl-L-leucyl)-1,3-thiazolidine-2-thione

Z-L-Leu-D-Ileu-OH
78569-25-2

Z-L-Leu-D-Ileu-OH

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran; water Ambient temperature;89%
9-methoxyacridine
10228-90-7

9-methoxyacridine

D-Isoleucine
319-78-8

D-Isoleucine

(2R,3R)-2-(Acridin-9-ylamino)-3-methyl-pentanoic acid

(2R,3R)-2-(Acridin-9-ylamino)-3-methyl-pentanoic acid

Conditions
ConditionsYield
In methanol for 10h; Heating;80%
D-Isoleucine
319-78-8

D-Isoleucine

azido-D-Ile

azido-D-Ile

Conditions
ConditionsYield
With triflic azide; potassium carbonate; copper(II) sulfate In methanol; dichloromethane; water at 20℃;73%
Stage #1: D-Isoleucine With triflic azide; potassium carbonate; copper(II) sulfate; potassium hydroxide In methanol; water for 8h; pH=8 - 10;
Stage #2: With sulfuric acid In water pH=3.5;
D-Isoleucine
319-78-8

D-Isoleucine

2-chloro-6-(naphthalen-2-yl)-4-phenylpyridine-3-carbonitrile

2-chloro-6-(naphthalen-2-yl)-4-phenylpyridine-3-carbonitrile

2-[3-cyano-6-(2-naphthyl)-4-phenylpyridin-2-ylamino]-3-methylpentanoic acid

2-[3-cyano-6-(2-naphthyl)-4-phenylpyridin-2-ylamino]-3-methylpentanoic acid

Conditions
ConditionsYield
With sodium carbonate In ethanol; water at 100℃; for 8h; pH=9 - 9.5;53%
D-Isoleucine
319-78-8

D-Isoleucine

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

benzyl alcohol
100-51-6

benzyl alcohol

D-isoleucine benzyl ester p-toluenesulfonate
80174-45-4

D-isoleucine benzyl ester p-toluenesulfonate

Conditions
ConditionsYield
In benzene at 70 - 115℃; for 5h; Dean-Stark;46%
D-Isoleucine
319-78-8

D-Isoleucine

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

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

C12H17N2O3(1+)

C12H17N2O3(1+)

Conditions
ConditionsYield
With triethylamine In methanol at 20℃; for 24h;35.2%
D-Isoleucine
319-78-8

D-Isoleucine

7-methoxycarbonylpterin
31010-69-2

7-methoxycarbonylpterin

(2R,3R)-2-(2-amino-4-oxo-3,4-dihydropteridine-7-carboxamido)-3-methylpentanoic acid

(2R,3R)-2-(2-amino-4-oxo-3,4-dihydropteridine-7-carboxamido)-3-methylpentanoic acid

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol at 20℃;19%
D-Fructose
57-48-7

D-Fructose

D-Isoleucine
319-78-8

D-Isoleucine

(R)-4-((R)-sec-butyl)-3-oxo-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6-carbaldehyde

(R)-4-((R)-sec-butyl)-3-oxo-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6-carbaldehyde

Conditions
ConditionsYield
With acetic acid; triethylamine at 80℃; for 8h;15.1%
Conditions
ConditionsYield
With hydrogenchloride
With hydrogenchloride at 100℃; for 0.5h;
With chloro-trimethyl-silane
(R)-2-bromopropionyl chloride
7148-74-5, 22592-73-0, 71425-59-7, 52152-04-2

(R)-2-bromopropionyl chloride

D-Isoleucine
319-78-8

D-Isoleucine

N-(2-bromo-propionyl)-isoleucine

N-(2-bromo-propionyl)-isoleucine

Conditions
ConditionsYield
With sodium hydroxide; diethyl ether ;
(R)-2-Bromo-4-methyl-pentanoyl chloride
28659-88-3, 59960-79-1, 104420-63-5

(R)-2-Bromo-4-methyl-pentanoyl chloride

D-Isoleucine
319-78-8

D-Isoleucine

N-(2-bromo-4-methyl-valeryl)-isoleucine
909874-75-5

N-(2-bromo-4-methyl-valeryl)-isoleucine

Conditions
ConditionsYield
With sodium hydroxide unter Eiskuehlung; ;
D-Isoleucine
319-78-8

D-Isoleucine

2-oxo-3(RS)-methylvaleric acid
1460-34-0

2-oxo-3(RS)-methylvaleric acid

Conditions
ConditionsYield
Aerobe oxydative Desaminierung unter der Einwirkung von D-Aminosaeure-Oxydase-Praeparaten aus tierischen Organen;
D-Isoleucine
319-78-8

D-Isoleucine

(2S)-2-methyl-1-butanol
1565-80-6

(2S)-2-methyl-1-butanol

Conditions
ConditionsYield
With Sucrose durch Reinzuchthefe;
D-Isoleucine
319-78-8

D-Isoleucine

(S)-2-Methylbutyric acid
1730-91-2

(S)-2-Methylbutyric acid

Conditions
ConditionsYield
durch Einw. von Faeulnisbakterien;
D-Isoleucine
319-78-8

D-Isoleucine

(3S)-methylvaleric acid
1730-92-3

(3S)-methylvaleric acid

Conditions
ConditionsYield
durch Einw. von Faeulnisbakterien;
Conditions
ConditionsYield
With barium dihydroxide at 180℃; aus dem enthaltenen Gemisch von d-Isoleucin und d-Alloisoleucin entfernt man das erstere durch Vergaeren mit Hefe in Gegenwart von Zucker; d-alloisoleucine;
D-Isoleucine
319-78-8

D-Isoleucine

(R)-3-methyl-2-oxovaleric acid
61748-89-8

(R)-3-methyl-2-oxovaleric acid

Conditions
ConditionsYield
With enzyme-substance from pig's kidney
D-Isoleucine
319-78-8

D-Isoleucine

N-formyl-isoleucine
4101-35-3, 89810-44-6

N-formyl-isoleucine

Conditions
ConditionsYield
durch Formylierung; formyl-d-isoleucine;
D-Isoleucine
319-78-8

D-Isoleucine

A

2-Methylbutylamine
96-15-1

2-Methylbutylamine

B

3,6-di-sec-butyl-piperazine-2,5-dione
35590-81-9, 35712-77-7, 39897-59-1, 142698-73-5, 142698-74-6

3,6-di-sec-butyl-piperazine-2,5-dione

D-Isoleucine
319-78-8

D-Isoleucine

(R)-2-methyl-butyraldehyde-(2,4-dinitro-phenylhydrazone)
33204-49-8

(R)-2-methyl-butyraldehyde-(2,4-dinitro-phenylhydrazone)

D-Isoleucine
319-78-8

D-Isoleucine

N-[(2,4-dichloro-phenoxy)-acetyl]-D-isoleucine
7407-67-2, 63905-57-7, 100937-49-3

N-[(2,4-dichloro-phenoxy)-acetyl]-D-isoleucine

319-78-8Relevant articles and documents

Rational engineering ofAcinetobacter tandoiiglutamate dehydrogenase for asymmetric synthesis ofl-homoalanine through biocatalytic cascades

Diao, Shiqing,Jiang, Shuiqin,Liu, Yan,Sun, Yangyang,Wang, Hualei,Wang, Liuzhu,Wei, Dongzhi

, p. 4208 - 4215 (2021/06/30)

l-Homoalanine, a useful building block for the synthesis of several chiral drugs, is generally synthesized through biocascades using natural amino acids as cheap starting reactants. However, the addition of expensive external cofactors and the low efficiency of leucine dehydrogenases towards the intermediate 2-ketobutyric acid are two major challenges in industrial applications. Herein, a dual cofactor-dependent glutamate dehydrogenase fromAcinetobacter tandoii(AtGluDH) was identified to help make full use of the intracellular pool of cofactors when using whole-cell catalysis. Through reconstruction of the hydrophobic network between the enzyme and the terminal methyl group of the substrate 2-ketobutyric acid, the strict substrate specificity ofAtGluDH towards α-ketoglutarate was successfully changed, and the activity obtained by the most effective mutant (K76L/T180C) was 17.2 times higher than that of the wild-type protein. A three-enzyme co-expression system was successfully constructed in order to help release the mass transfer restriction. Using 1 Ml-threonine, which is close to the solubility limit, we obtained a 99.9% yield ofl-homoalanine in only 3.5 h without adding external coenzymes to the cascade, giving 99.9% ee and a 29.2 g L?1h?1space-time yield. Additionally, the activities of the engineeredAtGluDH towards some other hydrophobic amino acids were also improved to 1.1-11.2 fold. Therefore, the engineering design of some dual cofactor-dependent GluDHs could not only eliminate the low catalytic activity of unnatural substrates but also enhance the cofactor utilization efficiency of these enzymes in industrial applications.

Enantioselective hydrogenation of cyclic tetrasubstituted-olefinic dehydroamino acid derivatives

Claverie, Jerome,Tang, Chuyan,Tang, Wenjun,Wan, Feng,Wang, Nan,Zhu, Yuxin

, p. 5546 - 5549 (2021/06/12)

An efficient asymmetric hydrogenation of cyclic tetrasubstituted-olefinic dehydroamino acid derivatives has been achieved with a Rh-ArcPhos catalyst, affording a series of α-acylamino-β-alkyl tetrahydropyranones with two contiguous chiral centers in up to 96% ee and 1000 TON.

Direct Synthesis of Free α-Amino Acids by Telescoping Three-Step Process from 1,2-Diols

Inada, Haruki,Shibuya, Masatoshi,Yamamoto, Yoshihiko

supporting information, p. 709 - 713 (2019/01/25)

A practical telescoping three-step process for the syntheses of α-amino acids from the corresponding 1,2-diols has been developed. This process enables the direct synthesis of free α-amino acids without any protection/deprotection step. This method was also effective for the preparation of a 15N-labeled α-amino acid. 1,2-Diols bearing α,β-unsaturated ester moieties afforded bicyclic α-amino acids through intramolecular [3 + 2] cycloadditions. A preliminary study suggests that the resultant α-amino acids are resolvable by aminoacylases with almost complete selectivity.

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