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74-79-3

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74-79-3 Usage

Indications and Usage

Odorless, slightly bitter. Easily soluble in water (solubility in 0℃ water is 83g/L, solubility in 50℃ water is 400g/L), very slightly soluble in ethanol, insoluble in ether; pI6.0; loses its 2-molecule water crystal when heated to 105℃, darkens in color at 230℃, disintegrates at 244℃; its aqueous solution has maximum absorption at 205nm (1gε3.28). L-Arginine is an encoding amino acid in protein synthesis and is one of the 8 essential amino acids in the human body. The body needs it for many different functions. Taking L-Arginine supplements can treat certain diseases such as congestive heart failure and cystitis. L-Arginine can also act as seasoning for nutrient supplements and food additives. L-Arginine can undergo a heat reaction with sugar (amino-carbonyl reaction) to obtain a unique fragrance, GB 2760-2001, an approved food spice. As an amino acid drug, L-Arginine can be used as pharmaceutical raw material and is an important ingredient in amino acid infusions and integrated amino acid preparations. It is also a crucial amino acid in maintaining infant growth and maturation.

Mechanisms of Action

L-Arginine can stimulate the human body to release certain chemicals such as insulin and human growth hormone. It can also clear ammonia in the body and promote the healing of wounds. The human body also needs it to produce sarcosine. Decomposing L-Arginine produces nitric oxide, which can expand blood vessels and increase blood flow. L-Arginine is an intermediate metabolite in the orthinine cycle and promotes the conversion of ammonia to urea, thus lowering the blood concentration of ammonia. L-Arginine is also an important part of sperm protein and can promote spermatogenesis and provide energy for sperm movement. Additionally, intravenous arginine can stimulate the pituitary to release growth hormone and can be used to test pituitary functions.

Adverse reactions

Abdominal pain, diarrhea, gout and bloating. There may also be increased severity in herpes breakouts and increased effects of antihypertensive drugs, resulting in a lower blood pressure than expected, which may cause hypertensive patients to experience dizziness and fainting.

Toxicity Level

Moderate

Acute Toxicity

Reference data: abdominal cavity – large rat LD50: 3793 mg/kg.

Flammability Characteristics

Flammable. Burning produces toxic nitrogen oxide smoke.

Handling

Store in ventilated, cool and dry area.

Extinguishers

Dry powder, foam, sand, carbon dioxide, water mist.

Chemical Properties

Different sources of media describe the Chemical Properties of 74-79-3 differently. You can refer to the following data:
1. Arginine is a diaminomonocarboxylic acid. The nonessential amino acid, arginine, is a urea cycle amino acid and a precursor for the neurotransmitter nitric oxide, which plays a role in the regulation of the brain’s system of dilation and constriction of small blood vessels. It is strongly alkaline and its water solutions absorb carbon dioxide from the air (FCC, 1996). Functionality in foods includes, but is not limited to, nutrient and dietary supplement
2. White crystalline powder

Occurrence

Reported present in cheese, chocolate, eggs, meat, nuts and other products.

Uses

Different sources of media describe the Uses of 74-79-3 differently. You can refer to the following data:
1. L-Arginine is used for heart and blood vessel conditions which includes congestive heart failure (CHF), chest pain, high blood pressure and coronary artery disease. It plays a vital role in the treatment of cardiovascular disease due to it being antiatherogenic, anti-ischemic, antiplatelet and antithrombotic. It acts as a growth stimulant and is involved in the treatment of erectile dysfunction in men. It is an important ingredient of tooth paste which provides effective relief for sensitive teeth.
2. Amino acid; nutrient.
3. L-Arginine has been used:as a Roswell park memorial institute medium (RPMI) media component in the isolation and culture of peripheral blood mononuclear cells (PBMCs)as a RPMI media component for tissue culturein DMEM medium for the identification and quantification of phosphorylation sites by stable isotope labeling by amino acids in cell culture (SILAC) and LCMS/MS

Definition

ChEBI: An L-alpha-amino acid that is the L-isomer of arginine.

Aroma threshold values

Detection at 100%, faint.

Taste threshold values

Taste characteristics at 1000 ppm: hint of sourness.

General Description

L-Arginine is an amino acid that plays a key role in many physiological processes such as tissue repair and reproduction. It is a key precursor for synthesizing nitric oxide in mammals. Due to these factors, the dietary supplementation with L-arginine may show a range of health benefits.

Biochem/physiol Actions

Substrate of nitric oxide synthase, which is converted to citrulline and nitric oxide (NO). Induces insulin release by a nitric oxide-dependent mechanism.

Safety Profile

Mutation data reported. Whenheated to decomposition it emits toxic fumes of NOx.

Synthesis

Enzymatically, arginine is formed in two reactions from citrulline. The first reaction (citrulline + succinate) is catalyzed by the enzyme arginosuccinate synthetase. It is ATP dependent and with the formation of a new C–N bond in the gaunidino group of arginosuccinate, water is removed and ATP is hydrolyzed. The second reaction is catalyzed by arginine synthetase and involves the scission of arginosuccinate with the formation of arginine and fumaric acid.

Purification Methods

S-Arginine crystallises from H2O as the dihydrate and as plates from EtOH. It also crystallises from 66% EtOH. Its solubility in H2O is 15% at 21o. Its isoelectric point is at pH 10.76. [Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 p 1841 1961, Beilstein 4 IV 817.]

Check Digit Verification of cas no

The CAS Registry Mumber 74-79-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 4 respectively; the second part has 2 digits, 7 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 74-79:
(4*7)+(3*4)+(2*7)+(1*9)=63
63 % 10 = 3
So 74-79-3 is a valid CAS Registry Number.
InChI:InChI=1/C6H14N4O2/c7-4(5(11)12)2-1-3-10-6(8)9/h4H,1-3,7H2,(H,11,12)(H4,8,9,10)/p+1/t4-/m0/s1

74-79-3 Well-known Company Product Price

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

  • (A0526)  L-(+)-Arginine  >99.0%(HPLC)(T)

  • 74-79-3

  • 25g

  • 145.00CNY

  • Detail
  • TCI America

  • (A0526)  L-(+)-Arginine  >99.0%(HPLC)(T)

  • 74-79-3

  • 100g

  • 295.00CNY

  • Detail
  • TCI America

  • (A0526)  L-(+)-Arginine  >99.0%(HPLC)(T)

  • 74-79-3

  • 500g

  • 1,100.00CNY

  • Detail
  • Alfa Aesar

  • (A15738)  L-Arginine, 98+%   

  • 74-79-3

  • 25g

  • 153.0CNY

  • Detail
  • Alfa Aesar

  • (A15738)  L-Arginine, 98+%   

  • 74-79-3

  • 100g

  • 284.0CNY

  • Detail
  • Alfa Aesar

  • (A15738)  L-Arginine, 98+%   

  • 74-79-3

  • 500g

  • 913.0CNY

  • Detail
  • Alfa Aesar

  • (A15738)  L-Arginine, 98+%   

  • 74-79-3

  • 2500g

  • 3877.0CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1106)  L-Arginine  pharmaceutical secondary standard; traceable to USP and PhEur

  • 74-79-3

  • PHR1106-1G

  • 732.19CNY

  • Detail
  • Sigma-Aldrich

  • (A1270000)  Arginine  European Pharmacopoeia (EP) Reference Standard

  • 74-79-3

  • A1270000

  • 1,880.19CNY

  • Detail
  • Sigma-Aldrich

  • (A5006)  L-Arginine  reagent grade, ≥98%

  • 74-79-3

  • A5006-100G

  • 552.24CNY

  • Detail
  • Sigma-Aldrich

  • (A5006)  L-Arginine  reagent grade, ≥98%

  • 74-79-3

  • A5006-500G

  • 1,501.11CNY

  • Detail
  • Sigma-Aldrich

  • (A5006)  L-Arginine  reagent grade, ≥98%

  • 74-79-3

  • A5006-1KG

  • 2,605.59CNY

  • Detail

74-79-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name L-arginine

1.2 Other means of identification

Product number -
Other names L-Arginine

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:74-79-3 SDS

74-79-3Synthetic route

Boc-Arg(Tos)-OH
13836-37-8

Boc-Arg(Tos)-OH

L-arginine
74-79-3

L-arginine

Conditions
ConditionsYield
With phenylthiotrimethylsilane; pertrimethylsilylated Nafion; 3-methyl-phenol; trifluoroacetic acid for 3h;100%
Z(OMe)-Arg(Mts)-OH
68262-73-7

Z(OMe)-Arg(Mts)-OH

L-arginine
74-79-3

L-arginine

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate; diphenyl sulfide In trifluoroacetic acid at 0℃; for 30h;100%
With trimethylsilyl trifluoromethanesulfonate; diphenyl sulfide In trifluoroacetic acid at 0℃; for 0.5h; Product distribution; New peptide deprotection procedure: hard-soft acid-base concept; the role of soft bases (thioanisole, dimethylsulfide, diphenylsulfide) employed; effect of var. hard bases; var. reaction cond.;100%
Nω-nitro-L-arginine
2149-70-4

Nω-nitro-L-arginine

L-arginine
74-79-3

L-arginine

Conditions
ConditionsYield
With phenylthiotrimethylsilane; pertrimethylsilylated Nafion; 3-methyl-phenol; trifluoroacetic acid for 3h;100%
cyclohexylammonium salt of Nα-benzyloxycarbonyl-NG-p-toluenesolfonyl-L-arginine
78221-85-9

cyclohexylammonium salt of Nα-benzyloxycarbonyl-NG-p-toluenesolfonyl-L-arginine

L-arginine
74-79-3

L-arginine

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; methoxybenzene In trifluoroacetic acid at 0℃; for 1h; Product distribution; various time, various temperature;100%
Fmoc-L-Arg-OH
91000-69-0

Fmoc-L-Arg-OH

L-arginine
74-79-3

L-arginine

Conditions
ConditionsYield
With sodium azide In N,N-dimethyl-formamide at 50℃; for 3h;95%
NG-Mds-Arg
75806-97-2

NG-Mds-Arg

L-arginine
74-79-3

L-arginine

Conditions
ConditionsYield
With methyl-phenyl-thioether; trifluoroacetic acid at 50℃; for 4h; Product distribution; deprotection of several NG-protected arginine derivatives;94.4%
Z(OMe)-Arg(MBS)-OH
67320-28-9

Z(OMe)-Arg(MBS)-OH

L-arginine
74-79-3

L-arginine

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate; methyl-phenyl-thioether In trifluoroacetic acid at 0℃; for 0.5h;93.5%
With trimethylsilyl trifluoromethanesulfonate; methyl-phenyl-thioether In trifluoroacetic acid at 0℃; for 0.5h; Product distribution; New peptide deprotection procedure: hard-soft acid-base concept; the role of soft bases (thioanisole, dimethylsulfide, diphenylsulfide) employed.;93.5%
Nα-Benzyloxycarbonyl-Nω-tosyl-L-arginin
13650-38-9

Nα-Benzyloxycarbonyl-Nω-tosyl-L-arginin

L-arginine
74-79-3

L-arginine

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate; methyl-phenyl-thioether In trifluoroacetic acid at 0℃; for 1h; Product distribution; New peptide deprotection procedure: hard-soft acid-base concept; the role of soft bases (thioanisole, dimethylsulfide, diphenylsulfide) employed.;86%
With trimethylsilyl trifluoromethanesulfonate; methyl-phenyl-thioether In trifluoroacetic acid at 0℃; for 0.5h;62.1%
5-[amino(iminomethyl)]amino-2-[(E,Z)-4,4,4-trichloro-3-oxo-1-butenylamino]pentanoic acid

5-[amino(iminomethyl)]amino-2-[(E,Z)-4,4,4-trichloro-3-oxo-1-butenylamino]pentanoic acid

L-arginine
74-79-3

L-arginine

Conditions
ConditionsYield
With hydrogenchloride In methanol at 70℃; for 20h;83%
5-[amino(iminomethyl)]amino-2-[(E,Z)-4,4,4-trifluoro-3-oxo-1-butenylamino]pentanoic acid

5-[amino(iminomethyl)]amino-2-[(E,Z)-4,4,4-trifluoro-3-oxo-1-butenylamino]pentanoic acid

L-arginine
74-79-3

L-arginine

Conditions
ConditionsYield
With hydrogenchloride In methanol at 70℃; for 20h;82%
(S)-4-(3-guanidinopropyl)-2,2-borabyciclo[3.3.1]nonane-1,3,2-oxazaborolidin-5-one

(S)-4-(3-guanidinopropyl)-2,2-borabyciclo[3.3.1]nonane-1,3,2-oxazaborolidin-5-one

L-arginine
74-79-3

L-arginine

Conditions
ConditionsYield
With hydrogenchloride In methanol; water at 20℃; for 0.5h; Inert atmosphere;74%
C6H14N4O2*H3N*ClH

C6H14N4O2*H3N*ClH

L-arginine
74-79-3

L-arginine

Conditions
ConditionsYield
With ruthenium nanoparticles dispersed in a polyvinylpyrrolidone matrix; amberlyst A-21 In methanol; dichloromethane68%
N5-[imino(nitroamino)methyl]-N2-[(phenylmethoxy)carbonyl]-L-ornithine
2304-98-5

N5-[imino(nitroamino)methyl]-N2-[(phenylmethoxy)carbonyl]-L-ornithine

L-arginine
74-79-3

L-arginine

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate; methyl-phenyl-thioether In trifluoroacetic acid at 0℃; for 0.5h;11%
Z-Arg(NO2)-OH

Z-Arg(NO2)-OH

L-arginine
74-79-3

L-arginine

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate; methyl-phenyl-thioether In trifluoroacetic acid at 0℃; for 0.5h; Product distribution; New peptide deprotection procedure: hard-soft acid-base concept; the role of soft bases (thioanisole, dimethylsulfide, diphenylsulfide) employed.;11%
Conditions
ConditionsYield
With barium dihydroxide; water
Conditions
ConditionsYield
Reaktion des Carbonats bei der Einw. von Leberpresssaft (Arginase);
Citrulline
372-75-8

Citrulline

L-arginine
74-79-3

L-arginine

Conditions
ConditionsYield
Ueber die enzymatische Bildung;
Nα-p-tosyl-L-arginine
1159-15-5

Nα-p-tosyl-L-arginine

L-arginine
74-79-3

L-arginine

Conditions
ConditionsYield
With hydrogen bromide; acetic acid; phenol
L-ornithine
70-26-8

L-ornithine

carbamimidothioic acid methyl ester
2986-19-8

carbamimidothioic acid methyl ester

L-arginine
74-79-3

L-arginine

Conditions
ConditionsYield
With barium dihydroxide
bromocyane
506-68-3

bromocyane

L-ornithine
70-26-8

L-ornithine

L-arginine
74-79-3

L-arginine

Conditions
ConditionsYield
Yield given. Multistep reaction;

A

D-arginine
157-06-2

D-arginine

B

L-arginine
74-79-3

L-arginine

Z-Arg-OH
1234-35-1

Z-Arg-OH

A

L-arginine
74-79-3

L-arginine

B

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
With cobalt(II); urethane hydrolase II at 33℃; for 2h; Product distribution; Kinetics; phosphate buffer pH 6.5;
L-arginine β-naphthylamide
7182-70-9, 13345-48-7

L-arginine β-naphthylamide

L-arginine
74-79-3

L-arginine

Conditions
ConditionsYield
With phosphate buffer; bovine leukocyte aminopeptidase (BL-APase) at 37℃; pH=7.0;
H-Arg(Mts)-OH
58810-06-3

H-Arg(Mts)-OH

L-arginine
74-79-3

L-arginine

Conditions
ConditionsYield
With methyl-phenyl-thioether; trifluoroacetic acid at 28℃; for 24h; Product distribution; var. reag.: dimethylsulfide, ethanedithiol, 2-mercaptoethanol; var. time;
bradykinin
58-82-2

bradykinin

A

L-arginine
74-79-3

L-arginine

B

des-Arg(9)-BK
15958-92-6

des-Arg(9)-BK

Conditions
ConditionsYield
With wheat carboxypeptidase from wheat bran at 30℃; Rate constant; pH 4.0; structure-reactivity relationship;
bradykinin
58-82-2

bradykinin

A

L-serin
56-45-1

L-serin

B

L-arginine
74-79-3

L-arginine

C

L-phenylalanine
63-91-2

L-phenylalanine

D

glycine
56-40-6

glycine

E

L-proline
147-85-3

L-proline

Conditions
ConditionsYield
With 155K Aspergillus oryzae ACID CPASE O at 30℃; for 1h; pH 3.7, release of C-terminal amino acid residues at longer incubation times;
Pyoverdine Pa

Pyoverdine Pa

L-arginine
74-79-3

L-arginine

Conditions
ConditionsYield
hydrolysis;
L-Tyrosyl-D-alanyl-glycyl-L-phenylalanyl-L-neopentylglycyl-L-arginine
126399-19-7

L-Tyrosyl-D-alanyl-glycyl-L-phenylalanyl-L-neopentylglycyl-L-arginine

A

L-arginine
74-79-3

L-arginine

B

L-Tyrosyl-D-alanyl-glycyl-L-phenylalanyl-L-neopentylglycine

L-Tyrosyl-D-alanyl-glycyl-L-phenylalanyl-L-neopentylglycine

Conditions
ConditionsYield
With TES buffer; carboxypeptidase B at 37℃; Product distribution; Determination of the rate of enzymatic degradation;
NG-2,2,5,7,8-pentamethylchroman-6-sulfonyl-L-arginine
112160-37-9

NG-2,2,5,7,8-pentamethylchroman-6-sulfonyl-L-arginine

L-arginine
74-79-3

L-arginine

Conditions
ConditionsYield
With hydrogen bromide In acetic acid for 0.0833333h; Ambient temperature;
With TFA - thioanisole; hydrogen bromide; acetic acid; trifluoroacetic acid for 2h; Product distribution; Ambient temperature;
3-(N-suberoylargininyl)hellebrigenin
105330-48-1

3-(N-suberoylargininyl)hellebrigenin

L-arginine
74-79-3

L-arginine

Conditions
ConditionsYield
With hydrogenchloride at 100℃; for 10h;
2-ethoxy-3-[4-{3-(4-methanesulfonyloxyphenyl)propylamino}phenyl]propionic acid

2-ethoxy-3-[4-{3-(4-methanesulfonyloxyphenyl)propylamino}phenyl]propionic acid

L-arginine
74-79-3

L-arginine

2-ethoxy-3-[4-{3-(4-methanesulfonyloxyphenyl) propylamino}phenyl]propionic acid arginine salt

2-ethoxy-3-[4-{3-(4-methanesulfonyloxyphenyl) propylamino}phenyl]propionic acid arginine salt

Conditions
ConditionsYield
In methanol at 20℃; for 2 - 3h;100%
(S)-2-methoxy-3-[4-{6-methanesulfonyloxynaphth-2-ylmethylamino}phenyl]propanoic acid

(S)-2-methoxy-3-[4-{6-methanesulfonyloxynaphth-2-ylmethylamino}phenyl]propanoic acid

L-arginine
74-79-3

L-arginine

(S)-2-methoxy-3-[4-{6-methanesulfonyloxynaphth-2-ylmethylamino}phenyl]propanoic acid arginine salt

(S)-2-methoxy-3-[4-{6-methanesulfonyloxynaphth-2-ylmethylamino}phenyl]propanoic acid arginine salt

Conditions
ConditionsYield
In methanol at 20℃; for 2 - 3h;100%
L-arginine
74-79-3

L-arginine

esomeprazole
119141-88-7

esomeprazole

esomeprazole L-arginine salt
942472-45-9

esomeprazole L-arginine salt

Conditions
ConditionsYield
In methanol; water100%
L-arginine
74-79-3

L-arginine

latanoprost acid
41639-83-2

latanoprost acid

latanoprost L-arginine salt
1224443-39-3

latanoprost L-arginine salt

Conditions
ConditionsYield
In methanol; water for 0.5h; Product distribution / selectivity;100%
In methanol; water for 0.5h; Product distribution / selectivity;
L-arginine
74-79-3

L-arginine

(+)-fluprostenol
54276-17-4

(+)-fluprostenol

arginyl (Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((R,E)-3-hydroxy-4-(3-(trifluoromethyl)phenoxy)but-1-enyl)cyclopentyl)hept-5-enoate
1224443-24-6

arginyl (Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((R,E)-3-hydroxy-4-(3-(trifluoromethyl)phenoxy)but-1-enyl)cyclopentyl)hept-5-enoate

Conditions
ConditionsYield
In methanol; water for 0.5h;100%
In methanol; water for 0.5h;
L-arginine
74-79-3

L-arginine

(R)-7-[3-amino-4-(2,4,5-trifluorophenyl)butanoyl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo [1,5-a]pyrazine-1-carboxylic acid

(R)-7-[3-amino-4-(2,4,5-trifluorophenyl)butanoyl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo [1,5-a]pyrazine-1-carboxylic acid

(R)-7-[3-amino-4-(2,4,5-trifluorophenyl)butanoyl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid (2S)-2-amino-5-guanidino-pentanoic acid

(R)-7-[3-amino-4-(2,4,5-trifluorophenyl)butanoyl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid (2S)-2-amino-5-guanidino-pentanoic acid

Conditions
ConditionsYield
In methanol; water for 4h;100%
L-arginine
74-79-3

L-arginine

(R)-7-[3-amino-4-(2,4,5-trifluorophenyl)-butyryl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo [1,5-a]pyrazine-1-carboxylic acid
1174122-63-4

(R)-7-[3-amino-4-(2,4,5-trifluorophenyl)-butyryl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo [1,5-a]pyrazine-1-carboxylic acid

(R)-7-[3-amino-4-(2,4,5-trifluorophenyl)-butyryl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo [1,5-a]pyrazine-1-carboxylic acid-(2S)-2-amino-5-carbamimidamidopentanoic acid
1242332-84-8

(R)-7-[3-amino-4-(2,4,5-trifluorophenyl)-butyryl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo [1,5-a]pyrazine-1-carboxylic acid-(2S)-2-amino-5-carbamimidamidopentanoic acid

Conditions
ConditionsYield
In methanol; water for 4h;100%
In methanol; water for 4h;100%
L-arginine
74-79-3

L-arginine

(S)-2-((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenamido)-4-methylpentanoic acid

(S)-2-((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenamido)-4-methylpentanoic acid

C6H14N4O2*C26H41NO3

C6H14N4O2*C26H41NO3

Conditions
ConditionsYield
In methanol at 20℃; for 2h;100%
L-arginine
74-79-3

L-arginine

4-{[(6-bromo-3-methyl-2-phenylquinolin-4-yl)carbonyl]amino}bicyclo[2.2.2]octane-1-carboxylic acid

4-{[(6-bromo-3-methyl-2-phenylquinolin-4-yl)carbonyl]amino}bicyclo[2.2.2]octane-1-carboxylic acid

4-{[(6-bromo-3-methyl-2-phenylquinolin-4-yl)carbonyl]amino}bicyclo[2.2.2]octane-1-carboxylic acid L-arginine salt

4-{[(6-bromo-3-methyl-2-phenylquinolin-4-yl)carbonyl]amino}bicyclo[2.2.2]octane-1-carboxylic acid L-arginine salt

Conditions
ConditionsYield
In ethanol; water Heating;100%
L-arginine
74-79-3

L-arginine

1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium-3-carboxylate
17720-18-2

1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium-3-carboxylate

1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium-3-carboxylate (S)-2-ammonio-5-guanidinopentanoate

1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium-3-carboxylate (S)-2-ammonio-5-guanidinopentanoate

Conditions
ConditionsYield
In water Cooling with ice;100%
L-arginine
74-79-3

L-arginine

nicotinic acid riboside 5'-monophosphate

nicotinic acid riboside 5'-monophosphate

(S)-1-carboxy-4-guanidinobutan-1-aminium 1-((2R,3R,4S,5R)-5-(((hydrogenphosphonato)oxy)methyl)-3,4-dihydroxyterahydrofuran-2-yl)pyridin-1-ium-3-carboxylate

(S)-1-carboxy-4-guanidinobutan-1-aminium 1-((2R,3R,4S,5R)-5-(((hydrogenphosphonato)oxy)methyl)-3,4-dihydroxyterahydrofuran-2-yl)pyridin-1-ium-3-carboxylate

Conditions
ConditionsYield
In water at 10℃; pH=Ca. 4.6 - 4.9;100%
L-arginine
74-79-3

L-arginine

nicotinic acid riboside 5'-monophosphate

nicotinic acid riboside 5'-monophosphate

bis((S)-1-carboxy-4-guanidinobutan-1-aminium)-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-((phosphonatooxy)methyl)tetrahydrofuran-2-yl)pyridin-1-ium-3-carboxylate

bis((S)-1-carboxy-4-guanidinobutan-1-aminium)-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-((phosphonatooxy)methyl)tetrahydrofuran-2-yl)pyridin-1-ium-3-carboxylate

Conditions
ConditionsYield
In water at 10℃; pH=Ca. 7 - 7.2;100%
nicotinic acid
59-67-6

nicotinic acid

L-arginine
74-79-3

L-arginine

L-arginine nicotinate

L-arginine nicotinate

Conditions
ConditionsYield
In water for 0.166667h; pH=Ca. 6 - 6.2; Cooling with ice;100%
(-)-3-[4-[2-(2,3-dihydro-1,4-benzothiazin-4-yl)ethoxy]phenyl]-2-ethoxypropanoic acid
223607-27-0

(-)-3-[4-[2-(2,3-dihydro-1,4-benzothiazin-4-yl)ethoxy]phenyl]-2-ethoxypropanoic acid

L-arginine
74-79-3

L-arginine

(-)-3-[4-[2-(2,3-dihydro-1,4-benzothiazin-4-yl)ethoxy]phenyl]-2-ethoxypropanoic acid, arginine salt
305827-56-9

(-)-3-[4-[2-(2,3-dihydro-1,4-benzothiazin-4-yl)ethoxy]phenyl]-2-ethoxypropanoic acid, arginine salt

Conditions
ConditionsYield
In ethanol; water at 20 - 50℃; for 10h;99.5%
L-arginine
74-79-3

L-arginine

C43H51N7O9S2

C43H51N7O9S2

(x)C6H14N4O2*C43H51N7O9S2

(x)C6H14N4O2*C43H51N7O9S2

Conditions
ConditionsYield
In methanol at 20℃;99.31%
L-arginine
74-79-3

L-arginine

nicotinic acid riboside 5'-monophosphate

nicotinic acid riboside 5'-monophosphate

(S)-1-carboxy-4-guanidinobutan-1-aminium ((2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

(S)-1-carboxy-4-guanidinobutan-1-aminium ((2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

Conditions
ConditionsYield
In water at 10℃; pH=Ca. 6.8 - 7;99%
L-arginine
74-79-3

L-arginine

1H,2H,2H-perfluoro-1-octyl succinic acid monoester
125111-32-2

1H,2H,2H-perfluoro-1-octyl succinic acid monoester

C12H9F13O4*C6H14N4O2

C12H9F13O4*C6H14N4O2

Conditions
ConditionsYield
In methanol; water Heating;99%
L-arginine
74-79-3

L-arginine

1H,1H,2H,2H-perfluoro-1-decyl succinic acid monoester

1H,1H,2H,2H-perfluoro-1-decyl succinic acid monoester

C14H9F17O4*C6H14N4O2

C14H9F17O4*C6H14N4O2

Conditions
ConditionsYield
In methanol; water Heating;99%
L-arginine
74-79-3

L-arginine

1H,1H,2H,2H-perfluoro-1-octyl glutaric acid monoester

1H,1H,2H,2H-perfluoro-1-octyl glutaric acid monoester

C13H11F13O4*C6H14N4O2

C13H11F13O4*C6H14N4O2

Conditions
ConditionsYield
In methanol; water Heating;99%
L-arginine
74-79-3

L-arginine

1H,1H,2H,2H-perfluoro-1-decyl glutaric acid monoester

1H,1H,2H,2H-perfluoro-1-decyl glutaric acid monoester

C15H11F17O4*C6H14N4O2

C15H11F17O4*C6H14N4O2

Conditions
ConditionsYield
In methanol; water Heating;99%
L-arginine
74-79-3

L-arginine

1H,1H,2H,2H-perfluoro-1-octylphthalic acid monoester

1H,1H,2H,2H-perfluoro-1-octylphthalic acid monoester

C16H9F13O4*C6H14N4O2

C16H9F13O4*C6H14N4O2

Conditions
ConditionsYield
In methanol; water Heating;99%
L-arginine
74-79-3

L-arginine

1H,1H,2H,2H-perfluoro-1-decyl phthalic acid monoester

1H,1H,2H,2H-perfluoro-1-decyl phthalic acid monoester

C18H9F17O4*C6H14N4O2

C18H9F17O4*C6H14N4O2

Conditions
ConditionsYield
In methanol; water Heating;99%
L-arginine
74-79-3

L-arginine

2-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)-malonic acid
36390-05-3

2-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)-malonic acid

2C6H14N4O2*C13H7F17O4

2C6H14N4O2*C13H7F17O4

Conditions
ConditionsYield
In methanol; water Heating;99%
L-arginine
74-79-3

L-arginine

3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-1-octa-6-thiohexanoic acid
220072-62-8

3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-1-octa-6-thiohexanoic acid

C14H15F13O2S*C6H14N4O2

C14H15F13O2S*C6H14N4O2

Conditions
ConditionsYield
In methanol; water for 2h; Reflux;99%
L-arginine
74-79-3

L-arginine

Ramipril
87333-19-5

Ramipril

ramipril-(L)-arginine

ramipril-(L)-arginine

Conditions
ConditionsYield
In water; isopropyl alcohol at 20℃; for 0.5h;98%
In butanone for 0.5h; Product distribution / selectivity; Heating / reflux;
L-arginine
74-79-3

L-arginine

salicylaldehyde
90-02-8

salicylaldehyde

L-salicylidenearginine

L-salicylidenearginine

Conditions
ConditionsYield
In ethanol for 12h; Reflux;98%
In methanol for 24.5h; Reflux;

74-79-3Relevant articles and documents

Binding Methylarginines and Methyllysines as Free Amino Acids: A Comparative Study of Multiple Host Classes**

Bayer, Peter,Hof, Fraser,Isaacs, Lyle,Kamba, Bianca E.,Le, My-Hue,Schrader, Thomas,Warmerdam, Zoey

, (2021/11/30)

Methylated free amino acids are an important class of targets for host-guest chemistry that have recognition properties distinct from those of methylated peptides and proteins. We present comparative binding studies for three different host classes that are each studied with multiple methylated arginines and lysines to determine fundamental structure-function relationships. The hosts studied are all anionic and include three calixarenes, two acyclic cucurbiturils, and two other cleft-like hosts, a clip and a tweezer. We determined the binding association constants for a panel of methylated amino acids using indicator displacement assays. The acyclic cucurbiturils display stronger binding to the methylated amino acids, and some unique patterns of selectivity. The two other cleft-like hosts follow two different trends, shallow host (clip) following similar trends to the calixarenes, and the other more closed host (tweezer) binding certain less-methylated amino acids stronger than their methylated counterparts. Molecular modelling sheds some light on the different preferences of the various hosts. The results identify hosts with new selectivities and with affinities in a range that could be useful for biomedical applications. The overall selectivity patterns are explained by a common framework that considers the geometry, depth of binding pockets, and functional group participation across all host classes.

Sequence-Selective Protection of Peptides from Proteolysis

Li, Xiaowei,Chen, Kaiqian,Zhao, Yan

supporting information, p. 11092 - 11097 (2021/04/05)

Proteolysis of proteins and peptides is involved in the infection of cells by enveloped viruses and also in the invasion and spread of cancer cells. Shutting down broad-specificity proteases, however, is problematic because normal functions by these proteases will be affected. Herein, nanoparticle receptors were prepared from molecular imprinting for complex biological peptides. Their strong and selective binding enabled them to protect their targeted sequences from proteolysis in aqueous solution at stoichiometric amounts. Generality of the method was demonstrated by the protection of hydrophobic and hydrophilic peptides from different proteases, selective protection of a segment of a long peptide, and selective protection of a targeted peptide in a mixture. Most interestingly, two receptors targeting different parts of a long peptide could work in cooperation to protect the overall sequence, highlighting the versatility of the method.

Development of a Raltegravir-based Photoaffinity-Labeled Probe for Human Immunodeficiency Virus-1 Integrase Capture

Pala, Nicolino,Esposito, Francesca,Tramontano, Enzo,Singh, Pankaj Kumar,Sanna, Vanna,Carcelli, Mauro,Haigh, Lisa D.,Satta, Sandro,Sechi, Mario

supporting information, p. 1986 - 1992 (2020/11/09)

Photoaffinity labeling (PAL) is one of the upcoming and powerful tools in the field of molecular recognition. It includes the determination of dynamic parameters, such as the identification and localization of the target protein and the site of drug binding. In this study, a photoaffinity-labeled probe for full-length human immunodeficiency virus-1 integrase (HIV-1 IN) capture was designed and synthesized, following the structure of the FDA-approved drug Raltegravir. This photoprobe was found to retain the HIV IN inhibitory potential in comparison with its parent molecule and demonstrates the ability to label the HIV-1 IN protein. Putative photoprobe/inhibitor binding sites near the catalytic site were then identified after protein digestion coupled to mass and molecular modeling analyses.

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