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3184-13-2

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3184-13-2 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 3184-13-2 differently. You can refer to the following data:
1. L(+)-Ornithine hydrochloride is white crystalline powder
2. White powder; mild green bark aroma.

Uses

Different sources of media describe the Uses of 3184-13-2 differently. You can refer to the following data:
1. Non-essential amino acid for human development but is required intermediate in arginine biosynthesis. Found in virtually all vertebrate tissues as well as incorporated into proteins, such as tyrocidine. Isolation from chicken excreta.
2. L(+)-Ornithine hydrochloride is a non-essential amino acid for human development but is required intermediate in arginine biosynthesis. L(+)-Ornithine hydrochloride is found in virtually all vertebrate tissues as well as incorporated into proteins, such as tyrocidine. Isolation from chicken excreta.
3. L(+)-Ornithine hydrochloride is a nonprotein amino acid used in the biosynthesis of L-arginine, L-proline and polyamines.

Aroma threshold values

Low strength odor, green type.

Taste threshold values

Very mild sweet taste at 500.00 ppm in water.

General Description

L-Ornithine is the functional metabolite of L-arginine.

Flammability and Explosibility

Notclassified

Biochem/physiol Actions

L-ornithine acts as a precursor for polyamines. It may modulate the intake of food as an acute satiety signal in the neonatal chick brain.

Safety Profile

Mildly toxic by ingestion. When heated to decomposition it emits very toxic fumes of NOx and HCl.

Purification Methods

Likely impurities are citrulline, arginine and D-ornithine. Crystallise the monohydrochloride from water by adding 4volumes of EtOH and dry it in a vacuum desiccator over fused CaCl2. [Rivard Biochemical Preparations 3 98 1955.] The dihydrochloride [6211-16-1] has m 202-203o and [ ] D +18.4o (c 2.3, 6N HCl) after recrystallisation from MeOH/Et2O [Zaoral & Rudinger Collect Czech Chem Commun 24 2009 1959]. [Beilstein 4 IV 2644.]

Check Digit Verification of cas no

The CAS Registry Mumber 3184-13-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,1,8 and 4 respectively; the second part has 2 digits, 1 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 3184-13:
(6*3)+(5*1)+(4*8)+(3*4)+(2*1)+(1*3)=72
72 % 10 = 2
So 3184-13-2 is a valid CAS Registry Number.
InChI:InChI=1/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)/p+1/t4-/m0/s1

3184-13-2 Well-known Company Product Price

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

  • (O0064)  L-Ornithine Monohydrochloride  >98.0%(HPLC)(T)

  • 3184-13-2

  • 25g

  • 225.00CNY

  • Detail
  • TCI America

  • (O0064)  L-Ornithine Monohydrochloride  >98.0%(HPLC)(T)

  • 3184-13-2

  • 250g

  • 1,240.00CNY

  • Detail
  • Alfa Aesar

  • (A12111)  L-Ornithine hydrochloride, 99%   

  • 3184-13-2

  • 25g

  • 132.0CNY

  • Detail
  • Alfa Aesar

  • (A12111)  L-Ornithine hydrochloride, 99%   

  • 3184-13-2

  • 100g

  • 328.0CNY

  • Detail
  • Alfa Aesar

  • (A12111)  L-Ornithine hydrochloride, 99%   

  • 3184-13-2

  • 500g

  • 1519.0CNY

  • Detail
  • Sigma

  • (O2375)  L-Ornithinemonohydrochloride  ≥99%

  • 3184-13-2

  • O2375-10MG

  • 190.71CNY

  • Detail
  • Sigma

  • (O2375)  L-Ornithinemonohydrochloride  ≥99%

  • 3184-13-2

  • O2375-5G

  • 301.86CNY

  • Detail
  • Sigma

  • (O2375)  L-Ornithinemonohydrochloride  ≥99%

  • 3184-13-2

  • O2375-25G

  • 345.15CNY

  • Detail
  • Sigma

  • (O2375)  L-Ornithinemonohydrochloride  ≥99%

  • 3184-13-2

  • O2375-100G

  • 837.72CNY

  • Detail
  • Sigma

  • (O2375)  L-Ornithinemonohydrochloride  ≥99%

  • 3184-13-2

  • O2375-1KG

  • 4,743.18CNY

  • Detail
  • Sigma

  • (O4386)  L-Ornithinemonohydrochloride  BioXtra, ≥99%

  • 3184-13-2

  • O4386-25G

  • 1,165.32CNY

  • Detail
  • Sigma

  • (O4386)  L-Ornithinemonohydrochloride  BioXtra, ≥99%

  • 3184-13-2

  • O4386-100G

  • 3,900.78CNY

  • Detail

3184-13-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name L(+)-Ornithine hydrochloride

1.2 Other means of identification

Product number -
Other names L-Ornithine, monohydrochloride

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:3184-13-2 SDS

3184-13-2Synthetic route

L-arginine hydrochloride
1119-34-2

L-arginine hydrochloride

A

L-ornithine hydrochloride
3184-13-2

L-ornithine hydrochloride

B

urea
57-13-6

urea

Conditions
ConditionsYield
With dipotassium hydrogenphosphate; phosphoric acid; water at 25 - 37.1℃; Thermodynamic data; ΔH; arginase (EC 3.5.3.1); var. pH and ionic strength;
L-ornithine tert-butyl ester
26302-89-6

L-ornithine tert-butyl ester

L-ornithine hydrochloride
3184-13-2

L-ornithine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride Heating;2.7 mmol
1,1-dimethylethyl 4-cyano-(2S)-[(diphenylmethylene)amino]butanoate
271601-28-6

1,1-dimethylethyl 4-cyano-(2S)-[(diphenylmethylene)amino]butanoate

L-ornithine hydrochloride
3184-13-2

L-ornithine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 96 percent / aq. citric acid / tetrahydrofuran / 3 h
2: H2 / platinum oxide / acetic acid / 16 h
3: 2.7 mmol / aq. HCl / Heating
View Scheme
tert-butyl 2-amino-4-cyanobutanoate
824956-17-4

tert-butyl 2-amino-4-cyanobutanoate

L-ornithine hydrochloride
3184-13-2

L-ornithine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2 / platinum oxide / acetic acid / 16 h
2: 2.7 mmol / aq. HCl / Heating
View Scheme
ethanol
64-17-5

ethanol

L-ornithine hydrochloride
3184-13-2

L-ornithine hydrochloride

L-ornithine, ethyl ester, hydrochloride
94231-37-5

L-ornithine, ethyl ester, hydrochloride

Conditions
ConditionsYield
With thionyl chloride at 0℃; Reflux;100%
phenylacetic acid
103-82-2

phenylacetic acid

L-ornithine hydrochloride
3184-13-2

L-ornithine hydrochloride

L-ornithine phenylacetate
952154-79-9

L-ornithine phenylacetate

Conditions
ConditionsYield
Stage #1: L-ornithine hydrochloride With calcium hydroxide In water for 0.5h;
Stage #2: phenylacetic acid In water Product distribution / selectivity;
100%
Stage #1: L-ornithine hydrochloride With acetic acid In water at 25 - 40℃; for 72h;
Stage #2: phenylacetic acid In water; isopropyl alcohol
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

L-ornithine hydrochloride
3184-13-2

L-ornithine hydrochloride

N,N-di-boc-ornithine
1154761-18-8

N,N-di-boc-ornithine

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; water for 12h;99%
L-ornithine hydrochloride
3184-13-2

L-ornithine hydrochloride

(3S)-3-aminopiperidin-2-one hydrochloride
42538-31-8

(3S)-3-aminopiperidin-2-one hydrochloride

Conditions
ConditionsYield
Stage #1: L-ornithine hydrochloride With chloro-trimethyl-silane In methanol at 20℃; under 760.051 Torr; for 12h;
Stage #2: With sodium ethanolate In methanol; ethanol at 0 - 20℃; under 760.051 Torr; for 0.583333h; enantioselective reaction;
97%
Multi-step reaction with 2 steps
1: SOCl2 / -15 - 20 °C
2: 2.25 mg / Et3N / acetonitrile / 4 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
2: 1.) sodium methylate, 2.) hydrochloric acid
View Scheme
Multi-step reaction with 2 steps
1: thionyl chloride / 3 h / 0 - 55 °C / Large scale
2: sodium carbonate / water / 12 h / 5 - 20 °C / Large scale
View Scheme
L-ornithine hydrochloride
3184-13-2

L-ornithine hydrochloride

L-ornithine methyl ester hydrochloride

L-ornithine methyl ester hydrochloride

Conditions
ConditionsYield
In methanol97%
In methanol97%
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

L-ornithine hydrochloride
3184-13-2

L-ornithine hydrochloride

(S)-5-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-aminopentanoic acid
147071-84-9

(S)-5-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-aminopentanoic acid

Conditions
ConditionsYield
Stage #1: L-ornithine hydrochloride With copper diacetate; sodium carbonate for 0.75h;
Stage #2: N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide In 1,4-dioxane; water for 0.75h; Further stages.;
96%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

L-ornithine hydrochloride
3184-13-2

L-ornithine hydrochloride

(S)-2,5-bis((tert-butoxycarbonyl)amino)pentanoic acid
57133-29-6

(S)-2,5-bis((tert-butoxycarbonyl)amino)pentanoic acid

Conditions
ConditionsYield
With triethylamine In water; acetone at 20℃; for 12h;96%
With sodium hydroxide In tetrahydrofuran at 20℃; for 3h;92%
With sodium hydroxide In tetrahydrofuran; water at 20℃; for 6h;85%
With sodium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 60h; pH=9;
L-carnitine
541-15-1

L-carnitine

L-ornithine hydrochloride
3184-13-2

L-ornithine hydrochloride

acetyl L-carnitine L-ornithate dihydrochloride

acetyl L-carnitine L-ornithate dihydrochloride

Conditions
ConditionsYield
In water at 40℃;96%
L-ornithine hydrochloride
3184-13-2

L-ornithine hydrochloride

(R)-(+)-3-Amino-2-piperidinon
88763-76-2

(R)-(+)-3-Amino-2-piperidinon

Conditions
ConditionsYield
With thionyl chloride In methanol at -80 - 25℃; for 24.5h;94.2%
Stage #1: L-ornithine hydrochloride With thionyl chloride In methanol at -45℃; for 1h;
Stage #2: In methanol at 20℃; for 19h;
63%
L-ornithine hydrochloride
3184-13-2

L-ornithine hydrochloride

4-aminobutyronitrile
32754-99-7

4-aminobutyronitrile

Conditions
ConditionsYield
With N-Bromosuccinimide In phosphate buffer; acetonitrile at 20℃; pH=5;94%
cetyl chloroformate
26272-90-2

cetyl chloroformate

L-ornithine hydrochloride
3184-13-2

L-ornithine hydrochloride

Nα,Nδ-bis(hexadecyloxycarbonyl)-L-ornithine
258875-29-5

Nα,Nδ-bis(hexadecyloxycarbonyl)-L-ornithine

Conditions
ConditionsYield
With sodium hydroxide In water; acetone for 48h; Acylation;93.4%
ethanol
64-17-5

ethanol

L-ornithine hydrochloride
3184-13-2

L-ornithine hydrochloride

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

Toluene-4-sulfonic acid; compound with (S)-2,5-diamino-pentanoic acid ethyl ester

Toluene-4-sulfonic acid; compound with (S)-2,5-diamino-pentanoic acid ethyl ester

Conditions
ConditionsYield
for 24h; Heating;93%
L-ornithine hydrochloride
3184-13-2

L-ornithine hydrochloride

benzyl chloroformate
501-53-1

benzyl chloroformate

(S)-2,5-bis-(benzyloxycarbonylamino)pentanoic acid
2274-58-0

(S)-2,5-bis-(benzyloxycarbonylamino)pentanoic acid

Conditions
ConditionsYield
With sodium carbonate In tetrahydrofuran at 20℃; Inert atmosphere;92%
With sodium hydroxide at 0℃; for 1h;85%
In water at 0℃; for 0.5h;
With sodium carbonate In 1,4-dioxane; water at 20℃; for 1h; pH=Ca. 10 - 11;7.1 g
With sodium carbonate In 1,4-dioxane; water at 20℃; for 1h; pH=10-11;7.1 g
L-ornithine hydrochloride
3184-13-2

L-ornithine hydrochloride

Conditions
ConditionsYield
With aluminum oxide; sodium hydroxide In toluene for 1.5h; Heating;90%
With aluminum oxide; sodium hydroxide In water; toluene Reflux;
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

copper(II) acetate monohydrate
6046-93-1

copper(II) acetate monohydrate

L-ornithine hydrochloride
3184-13-2

L-ornithine hydrochloride

copper(II) complex of Nδ-tert-butoxycarbonyl-L-ornithine

copper(II) complex of Nδ-tert-butoxycarbonyl-L-ornithine

Conditions
ConditionsYield
With sodium hydroxide In water90%
choline
62-49-7

choline

L-ornithine hydrochloride
3184-13-2

L-ornithine hydrochloride

C5H14NO(1+)*C5H11N2O2(1-)

C5H14NO(1+)*C5H11N2O2(1-)

Conditions
ConditionsYield
In water at 100℃; for 3h;85%
L-ornithine hydrochloride
3184-13-2

L-ornithine hydrochloride

benzyl chloroformate
501-53-1

benzyl chloroformate

N-carboxybenzyl-L-ornithine
3304-51-6

N-carboxybenzyl-L-ornithine

Conditions
ConditionsYield
Stage #1: L-ornithine hydrochloride With copper(II) sulfate; sodium hydroxide for 0.25h;
Stage #2: benzyl chloroformate With potassium carbonate
83%
Stage #1: L-ornithine hydrochloride With sodium hydroxide In water
Stage #2: With copper(ll) sulfate pentahydrate In water for 0.25h;
Stage #3: benzyl chloroformate Further stages;
82%
Stage #1: L-ornithine hydrochloride In water for 0.5h; complexation; Heating;
Stage #2: benzyl chloroformate With magnesium oxide In tetrahydrofuran; water at 20℃; for 22h; Acylation;
Stage #3: With ethylenediaminetetraacetic acid; sodium hydrogencarbonate In water for 2h; decomplexation; Heating;
58%
benzyl-8-quinolyl carbonate
19506-72-0

benzyl-8-quinolyl carbonate

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

L-ornithine hydrochloride
3184-13-2

L-ornithine hydrochloride

Z-Orn(Boc)-OH
7733-29-1

Z-Orn(Boc)-OH

Conditions
ConditionsYield
Acylation; Multistep reaction;82%
ethyl trifluoroacetate,
383-63-1

ethyl trifluoroacetate,

L-ornithine hydrochloride
3184-13-2

L-ornithine hydrochloride

(S)-N,N'-bis(trifluoroacetyl)ornithine
863991-44-0

(S)-N,N'-bis(trifluoroacetyl)ornithine

Conditions
ConditionsYield
With triethylamine In methanol at 20℃; for 48h;81.03%
L-ornithine hydrochloride
3184-13-2

L-ornithine hydrochloride

2-methylsulfonyl ethyloxycarbonyl chloride
53298-29-6

2-methylsulfonyl ethyloxycarbonyl chloride

H-Orn(Msc)-OH
77549-19-0

H-Orn(Msc)-OH

Conditions
ConditionsYield
With sodium hydroxide; copper(I) sulfate In tetrahydrofuran; water80%
L-ornithine hydrochloride
3184-13-2

L-ornithine hydrochloride

(S)-(-)-3-aminopiperidin-2-one
34294-79-6

(S)-(-)-3-aminopiperidin-2-one

Conditions
ConditionsYield
With sodium hydrogencarbonate In water for 1h; Microwave irradiation;78%
With thionyl chloride In methanol at -78 - 20℃;77%
Multi-step reaction with 2 steps
1: SOCl2 / 22 h / 0 - 20 °C
2: aq. NaHCO3 / 15 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: HCl gas / 2 h / Heating
2: NaOMe / methanol / 2 h / 20 °C
View Scheme
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

L-ornithine hydrochloride
3184-13-2

L-ornithine hydrochloride

3(S)-<(butoxycarbonyl)amino>-2-oxopiperidine
92235-39-7

3(S)-<(butoxycarbonyl)amino>-2-oxopiperidine

Conditions
ConditionsYield
Stage #1: L-ornithine hydrochloride With hydrogenchloride In methanol at 20℃; for 4.75h;
Stage #2: With sodium methylate In methanol at 20℃; for 4h;
Stage #3: di-tert-butyl dicarbonate With triethylamine In dichloromethane at 20 - 25℃; for 60h;
78%
pyridine
110-86-1

pyridine

Pyridine-2,6-dicarboxylic acid
499-83-2

Pyridine-2,6-dicarboxylic acid

cerium(III) nitrate hexahydrate

cerium(III) nitrate hexahydrate

water
7732-18-5

water

L-ornithine hydrochloride
3184-13-2

L-ornithine hydrochloride

7H2O*C5H5N*C21H9CeN3O12(3-)*3H(1+)*C5H12N2O2

7H2O*C5H5N*C21H9CeN3O12(3-)*3H(1+)*C5H12N2O2

Conditions
ConditionsYield
Stage #1: Pyridine-2,6-dicarboxylic acid; cerium(III) nitrate hexahydrate In methanol for 0.5h;
Stage #2: pyridine; water; L-ornithine hydrochloride In methanol
78%
C14H15N5O2S

C14H15N5O2S

L-ornithine hydrochloride
3184-13-2

L-ornithine hydrochloride

N-omega-(1,2-dimethylindole-3-sulfonyl)-L-arginine
1177425-22-7

N-omega-(1,2-dimethylindole-3-sulfonyl)-L-arginine

Conditions
ConditionsYield
Stage #1: L-ornithine hydrochloride With lithium hydroxide monohydrate In water at 30 - 50℃; for 0.5h; Large scale;
Stage #2: C14H15N5O2S In water; acetonitrile at 60℃; for 16h; Large scale;
Stage #3: With copper(II) chloride monohydrate In water; acetonitrile at 60℃; for 5h; Large scale;
78%
L-ornithine hydrochloride
3184-13-2

L-ornithine hydrochloride

(3S)-Aminopiperidin-2-one
31967-09-6

(3S)-Aminopiperidin-2-one

Conditions
ConditionsYield
With thionyl chloride In methanol; chloroform77%
With thionyl chloride In methanol; chloroform; water69%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

L-ornithine hydrochloride
3184-13-2

L-ornithine hydrochloride

Nδ-(tert-butoxycarbonyl)-L-ornithine
13650-49-2

Nδ-(tert-butoxycarbonyl)-L-ornithine

Conditions
ConditionsYield
Stage #1: L-ornithine hydrochloride With copper(II) carbonate In water for 2h; Reflux;
Stage #2: di-tert-butyl dicarbonate With sodium hydrogencarbonate In water; acetone at 20℃;
70%
Yield given. Multistep reaction;
Multistep reaction;
Iodoacetic acid 4-nitrophenyl ester
31252-85-4

Iodoacetic acid 4-nitrophenyl ester

L-ornithine hydrochloride
3184-13-2

L-ornithine hydrochloride

(+)-S-2-amino-5-iodoacetamidopentanoic acid
35748-65-3

(+)-S-2-amino-5-iodoacetamidopentanoic acid

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran at 4℃; for 5h;70%
cobalt(II) chloride hexahydrate

cobalt(II) chloride hexahydrate

2,2',2''-triaminotriethylamine
4097-89-6

2,2',2''-triaminotriethylamine

L-ornithine hydrochloride
3184-13-2

L-ornithine hydrochloride

(tris(2-aminoethyl)amine-ornithine)cobalt(III) trichloride trihydrate

(tris(2-aminoethyl)amine-ornithine)cobalt(III) trichloride trihydrate

Conditions
ConditionsYield
With NaOH; H2O2; activated charcoal In water addn. of N(CH2CH2NH2)3, NaOH and activated charcoal to soln. of CoCl2*6H2O and NH2(CH2)3CH(NH2)COOH*HCl in H2O, addn. of 28% H2O2 in small portions over 1 h, addn. of 3.0 M HCl, stirring for 1 h; filtration, dilution of filtrate, chromy., washing with water, elution with 3.0 M HCl, evapn. to dryness, dissolving in min. amt. of hot HCl, addn. of ethanol, crystn. at 5°C, collection, washing with EtOH anddiethyl ether, elem. anal.;64%
L-ornithine hydrochloride
3184-13-2

L-ornithine hydrochloride

acrylonitrile
107-13-1

acrylonitrile

Nα,Nδ,Nδ-tris(2-cyanoethyl)ornithine hydrochloride

Nα,Nδ,Nδ-tris(2-cyanoethyl)ornithine hydrochloride

Conditions
ConditionsYield
With sodium hydroxide In methanol at 20℃; for 24h; Michael addition;62%
cis,trans-2,5-dimethoxytetrahydrofuran
696-59-3

cis,trans-2,5-dimethoxytetrahydrofuran

L-ornithine hydrochloride
3184-13-2

L-ornithine hydrochloride

(S)-2,5-di(1H-pyrrol-1-yl)pentanoic acid
1239733-08-4

(S)-2,5-di(1H-pyrrol-1-yl)pentanoic acid

Conditions
ConditionsYield
Stage #1: L-ornithine hydrochloride With sodium acetate; acetic acid In 1,2-dichloro-ethane at 90℃; for 0.0833333h;
Stage #2: cis,trans-2,5-dimethoxytetrahydrofuran In 1,2-dichloro-ethane at 90℃;
62%
Stage #1: L-ornithine hydrochloride With sodium acetate; acetic acid In water; 1,2-dichloro-ethane at 80℃; for 0.166667h;
Stage #2: cis,trans-2,5-dimethoxytetrahydrofuran In water; 1,2-dichloro-ethane at 80℃;
26%

3184-13-2Relevant articles and documents

Thermochemistry of the hydrolysis of L-arginine to (L-citrulline + ammonia) and of the hydrolysis of L-arginine to (L-ornithine + urea)

Tewari, Y. B.,Kishore, N.,Margolis, S. A.,Goldberg, R. N.,Shibatani, T.

, p. 293 - 305 (1993)

Molar enthalpies of reaction for the hydrolysis of L-arginine(aq) to and for the hydrolysis of L-arginine(aq) to have been measured by microcalorimetry.These reactions are catalyzed, respectively, by arginase and by arginine deiminase.The effects of variations in pH, temperature, and ionic strength on the molar enthalpies of reaction were studied.The results have been analyzed with a model which accounts for the complex equilibria in solution.The results obtained at T = 298.15 K for the reference reactions are: ΔfHm0 = -(21.4+/-0.5) kJ * mol-1 for L-arginine+(aq) + H2O(l) = L-ornithine+(aq) + urea(aq) and ΔfHm0 = -(31.9+/-0.8) kJ * mol-1 for L-arginine+(aq) + H2O(l) = L-citrulline(aq) + NH4+(aq).These results are discussed in terms of thermodynamic-cycle calculations and in terms of the metabolic urea cycle.

Synthesis of (ε-13C-,ε-15N)-enriched L-lysine - Establishing schemes for the preparation of all possible 13C and 15N isotopomers of L-lysine, L-ornithine, and L-proline

Siebum, Arjan H. G.,Tsang, Robert K. F.,Van Der Steen, Rob,Raap, Jan,Lugtenburg, Johan

, p. 4391 - 4396 (2007/10/03)

In this paper we describe a simple synthetic strategy that, with the right rational adaptation, gives direct access to any 13C/15N isotopomer of L-glutamate, L-ornithine, L-proline, L-lysine, and L-α, amino adipic acid. This strategy also allows access to nonproteinogenic amino acids like L-citrulline in high yields and optical purity. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Aminosaeuren, I. Darstellung von Aminosaeuren aus Halogencarbonsaeure-alkylestern mit Alkalimetallcyanaten

Effenberger, Franz,Drauz, Karlheinz,Foerster, Siegfried,Mueller, Wolfgang

, p. 173 - 189 (2007/10/02)

α- and ω-halo- as well as α,ω-dihalocarboxylic alkyl esters react with potassium cyanate in the presence of alcohol at 80 - 120 deg C in dipolar aprotic solvents to yield α- and ω-(alkoxycarbonylamino)- and α,ω-bis(alkoxycarbonylamino)carboxylic alkyl esters, respectively, in good yields.Hydrolytic cleavage of these mono- or diurethanes with an aqueous solution of hydrochloric acid/formic acid leads to the corresponding amino acid hydrochlorides in nearly quantitative yields.

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