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L-Lysine

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Name

L-Lysine

EINECS 200-294-2
CAS No. 56-87-1 Density 1.125 g/cm3
PSA 89.34000 LogP 0.92790
Solubility water: 0.1 g/mL, clear, colorless Melting Point 215 °C (dec.)(lit.)
Formula C6H14N2O2 Boiling Point 311.542 °C at 760 mmHg
Molecular Weight 146.22 Flash Point 142.216 °C
Transport Information Appearance white or almost white crystalline powder
Safety 24/25 Risk Codes
Molecular Structure Molecular Structure of 56-87-1 (L-Lysine) Hazard Symbols IrritantXi
Synonyms

Hexanoic acid, 2,6-diamino-, (S)-;Lys;Aminutrin;Lysine, L- (8CI);Aminutrin, 6-amino-;L-Lysine (USAN);(S)-lysine;(S)-alpha,epsilon-diaminocaproic acid;L-Lysine (9CI);(S)-2,6-diaminohexanoic acid;h-Lys-oh;2,6-Diaminohexanoic acid, (S)-;L-Lysin;L-(+)-Lysine;L-Norleucine, 6-amino-;Lysine acid;Lysine, L-;alpha-Lysine;LYS (IUPAC abbreviation);L-Lysine Base;L-Lysine Free Base;L-Lysine alkali;L-Lysine Feed Grade;L-Lysine,L-Glutamic acid,L-Arginine,L-Cystine;Lysine;(S)-(+)-Lysine;L -lysine;L-Lysine 50% Solution;

 

L-Lysine Synthetic route

2389-45-9

Boc-Lys(Z)-OH

56-87-1

L-lysine

Conditions
ConditionsYield
With dimethylsulfide; hydrogen fluoride at 0℃; for 2h; Product distribution; Var.: HF in anisole;100%
54613-99-9

Boc-(S)-Lys(2-Cl-Z)-OH

56-87-1

L-lysine

Conditions
ConditionsYield
With Nafion H; dimethylsulfide; 3-methyl-phenol; trifluoroacetic acid for 3h;100%
83031-06-5

H-Lys(Mtr)-OH

56-87-1

L-lysine

Conditions
ConditionsYield
With methanesulfonic acid; methanesulfonic acid in trifluoroacetic acid-thioanisole; trifluoroacetic acid at 20℃; for 2h; Product distribution; effect of the concentration of methanesulfonic acid; deprotection of the Mtr group with various deprotecting agents (TFA-thioanisole, HF-thioanisole, TFA, methanesulfonic acid-thioanisole);99.3%
With methanesulfonic acid; dimethylsulfide; TFA-thioanisole at 20℃; for 1h; Product distribution; in the presence or absence of methyl sulfide; variation of MSA concentration and time;98.9%
With methanesulfonic acid; dimethylsulfide; methyl-phenyl-thioether; trifluoroacetic acid at 20℃; for 1h; Yield given;
With methanesulfonic acid In trifluoroacetic acid at 20℃; for 2h;
42533-12-0

Z(OMe)-Lys(Z)-OH

56-87-1

L-lysine

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate; methyl-phenyl-thioether In trifluoroacetic acid at 0℃; for 0.5h;98.7%
With trimethylsilyl trifluoromethanesulfonate; methyl-phenyl-thioether In trifluoroacetic acid at 0℃; for 0.5h; Product distribution; further protected amino acids; var. of reagents, temperature and time;98.7%
With trimethylsilyl trifluoromethanesulfonate; methyl-phenyl-thioether In trifluoroacetic acid at 22℃; for 1h; 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.;98.7%
With trimethylsilyl trifluoromethanesulfonate; methyl-phenyl-thioether In trifluoroacetic acid for 0.5h; Product distribution; var. other protected amino acids; var. protecting groups;98.7%
2212-75-1

N2-[(benzyloxy)carbonyl]-L-lysine

56-87-1

L-lysine

Conditions
ConditionsYield
With hydrogen; hydroxyapatite-bound Pd In methanol at 40℃; for 3h;93%
With sodium tetrahydroborate In methanol; aq. phosphate buffer at 20℃; for 2h; Cooling with ice; Sealed tube;90%
With formic acid; palladium In methanol
With cell extract of Sphingomonas paucimobilis SC 16113 In water at 42℃; for 20h; Enzymatic reaction;98 % Chromat.
With ethylenediaminetetraacetic acid; phenylmethylsulphonyl fluoride; water In aq. phosphate buffer at 30℃; Kinetics; Reagent/catalyst; Microbiological reaction; Enzymatic reaction;
2483-46-7

Boc-Lys(Boc)-OH

56-87-1

L-lysine

Conditions
ConditionsYield
With tetradecyl(trihexyl)phosphonium bistriflamide; trifluoroacetic acid at 130℃; for 0.183333h; Ionic liquid;93%
Multi-step reaction with 3 steps
1: dicyclohexyl-carbodiimide / dichloromethane / 20 °C
2: hydrogen bromide; acetic acid / 2 h / 20 °C
3: Pseudomonas aeruginosa ORF PA0919; mono-p-nitrophenyl phosphate / dimethyl sulfoxide; aq. phosphate buffer / 22 °C / pH 6.8
View Scheme
Boc-Lys-Merrifield resin

Boc-Lys-Merrifield resin

56-87-1

L-lysine

Conditions
ConditionsYield
With dimethyl ether-poly(hydrogen fluoride) at 0℃; for 1h;91%

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

56-87-1

L-lysine

Conditions
ConditionsYield
With hydrogenchloride In methanol; water at 20℃; for 0.5h; Inert atmosphere;91%
105047-45-8

Fmoc-Lys-OH

56-87-1

L-lysine

Conditions
ConditionsYield
With sodium azide In N,N-dimethyl-formamide at 50℃; for 4h;90%
405-39-0

N,N'-di-[(phenylmethoxy)carbonyl]-L-lysine

56-87-1

L-lysine

Conditions
ConditionsYield
With hydrogen; hydroxyapatite-bound Pd In methanol at 40℃; for 12h;88%
With cell extract of Sphingomonas paucimobilis SC 16113 In water at 42℃; for 20h; Enzymatic reaction;72 % Chromat.

C6H14N2O2*H3N*ClH

56-87-1

L-lysine

Conditions
ConditionsYield
With ruthenium nanoparticles dispersed in a polyvinylpyrrolidone matrix; amberlyst A-21 In methanol; dichloromethane82%
71-23-8

propan-1-ol

4117-33-3

L-Lysine ethyl ester

A

56-87-1

L-lysine

B

57590-09-7

L-lysine n-propyl ester

Conditions
ConditionsYield
immobilized trypsin at 25℃; 5percent 0.1 M acetate buffer, pH:6.2;A n/a
B 80%
64-17-5

ethanol

57590-09-7

L-lysine n-propyl ester

A

4117-33-3

L-Lysine ethyl ester

B

56-87-1

L-lysine

Conditions
ConditionsYield
immobilized trypsin at 25℃; 5percent 0.1 M acetate buffer, pH:6.2;A 80%
B n/a

N4-lysylsulfanilamide dihydrochloride

56-87-1

L-lysine

Conditions
ConditionsYield
With trypsin In water for 24h; Product distribution; several reaction times;60%
23931-59-1

Nα-formyl-Nε-(desoxy-1-D-fructosyl-1)-L-lysine

A

56-87-1

L-lysine

B

furosine

furosine

Conditions
ConditionsYield
With hydrogenchloride at 115℃; for 18h; Product distribution; also influence of D-glucose;A 35%
B n/a
6404-26-8

(S)-6-acetamido-2-((tertbutoxycarbonyl)amino)hexanoic acid

122890-70-4

1,1-bis(4-aminophenyl)-2,2-diphenylethene

A

56-87-1

L-lysine

B

C39H44N4O4

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 5h; Inert atmosphere;A n/a
B 12%
124-83-4

D-(+)-camphoric acid

56-87-1

L-lysine

Conditions
ConditionsYield
With (-)-(R,R)-dibenzoyltartaric acid
With N-acetyl-3,5-dibromo-L-tyrosine
With L-glutamic acid
542-32-5

(R,S)-2-aminoadipic acid

56-87-1

L-lysine

Conditions
ConditionsYield
Herstellung mit Hilfe von Backhefe oder von Torulopsis utilis;
50-99-7

D-glucose

56-87-1

L-lysine

Conditions
ConditionsYield
With ammonium chloride Herstellung mit Hilfe von Micrococcus glutamicus;
With PO4 Herstellung mit Hilfe von Ustilago maydis;
5107-18-6

N6-benzoyl-lysine

56-87-1

L-lysine

Conditions
ConditionsYield
Herstellung mit Hilfe eines Enzym-Praeparats aus Pseudomonas;
3066-80-6

N2-acetyl-N6-benzoyl-DL-lysine

56-87-1

L-lysine

Conditions
ConditionsYield
Herstellung mit Hilfe eines Enzym-Praeparats aus Aspergillus oryzae;
67-56-1

methanol

A

72-19-5

L-threonine

B

56-87-1

L-lysine

C

56-84-8

L-Aspartic acid

D

56-86-0

L-glutamic acid

Conditions
ConditionsYield
at 30℃; for 72h; Product distribution; time-course, Methylobacillus glycogenes ATCC 21371 (ATR80) mutant, other mutants, other strains;
50-00-0

formaldehyd

Nε-hydroxymethyllysine

56-87-1

L-lysine

Conditions
ConditionsYield
In water-d2 at 25℃; Equilibrium constant; effect of the pH;
1118-90-7

L-homoglutamic acid

56-87-1

L-lysine

Conditions
ConditionsYield
at 30℃; pH 6.0; Saccaromyces cerevisiae strain AJI4599; other strains;
1155-64-2

N6-[(benzyloxy)carbonyl]-L-lysine

56-87-1

L-lysine

Conditions
ConditionsYield
With methyl-phenyl-thioether In trifluoroacetic acid at 25℃; for 3h; Yield given;
With trifluoroacetic acid In dichloromethane at 20℃; Rate constant;
With methyl-phenyl-thioether; trifluoroacetic acid at 25℃; Product distribution; conversion as a function of time, also in the case of other reagents: TFA/DMSO, TFA/anisole;
With methyl-phenyl-thioether; trifluoroacetic acid at 28℃; for 24h; Product distribution; var. reag.: dimethylsulfide, ethanedithiol, 2-mercaptoethanol; var. time;
With cell extract of Sphingomonas paucimobilis SC 16113 In water at 42℃; for 20h; Enzymatic reaction;98 % Chromat.
740-63-6

Nα-benzoyl-glycyl-L-lysine

A

495-69-2

Hippuric Acid

B

56-87-1

L-lysine

Conditions
ConditionsYield
With wheat carboxypeptidase from wheat bran at 30℃; Rate constant; pH 4.0; structure-reactivity relationship;
3844-53-9

L-lysine ethyl ester dihydrochloride

A

997-20-6

lysine tetrapeptide

B

19431-21-1

poly(L-lysine), 5-mer

C

56-87-1

L-lysine

D

13184-13-9

dilysine

E

13184-14-0

Lys-Lys-Lys

F

554-38-1

hexalysine

Conditions
ConditionsYield
multistep reaction; 1.) trypsin, Na2CO3 buffer pH 10.0, 25 deg C, 2.) NaOH, 60 deg C, 15 min; trypsin-catalyzed oligomerization of L-lysine esters, pH-dependence, reaction rate, kinetics, effect of NaCl; other L-lysin alkyl esters, enzyme or amino acids;
Conditions
ConditionsYield
Stage #1: methanol With thionyl chloride at 0℃; for 0.166667h;
Stage #2: L-lysine at 0℃; for 3.16667h; Reflux;
100%
Stage #1: methanol With thionyl chloride at 0℃;
Stage #2: L-lysine at 0 - 80℃; for 1.66667h;
96%
With hydrogenchloride87%
Stage #1: methanol; L-lysine With thionyl chloride at 0℃; Reflux;
Stage #2: With hydrogenchloride
85.8%
Stage #1: methanol With thionyl chloride at 0℃; for 0.5h;
Stage #2: L-lysine Heating;
56-87-1

L-lysine

154357-42-3

S-(-)-9-fluoro-6,7-dihydro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-1H,5H-benzo[i,j]quinolizine-2-carboxylic acid

S-(-)-9-fluoro-6,7-dihydro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-1H,5H-benzo[i,j]quinolizine-2-carboxylic acid L-lysine salt

Conditions
ConditionsYield
In methanol; water at 65 - 70℃; for 0.25h; Product distribution / selectivity;100%
In water; acetone at 70℃; for 1h; Product distribution / selectivity;
56-87-1

L-lysine

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

(S)-2,6-diammoniohexanoate (S)-2-((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenamido)-4-methylpentanoate

Conditions
ConditionsYield
In methanol at 20℃; for 2h;100%
56-87-1

L-lysine

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-lysine salt

Conditions
ConditionsYield
In ethanol; water Heating;100%
67-56-1

methanol

56-87-1

L-lysine

lysine methyl ester hydrochloride

Conditions
ConditionsYield
With thionyl chloride at 0℃; for 0.333333h;100%
56-87-1

L-lysine

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)-6-amino-2-ammoniohexanoate

Conditions
ConditionsYield
In water pH=9.63; Cooling with ice;100%
56-87-1

L-lysine

1094-61-7

nicotinamide mononucleotide

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

Conditions
ConditionsYield
In water at 10℃; pH=Ca. 6 - 6.2;100%
56-87-1

L-lysine

54207-61-3

3,3,4,4,5,5,6,6,7,7,8,8,8,9,10,10,10,10-heptadecafluoro-1-decathioacetic acid

C12H7F17O2S*C6H14N2O2

Conditions
ConditionsYield
In methanol; water for 2h; Reflux;100%
56-87-1

L-lysine

3,3,4,4,5,5,6,6,7,7,8,8,9,9,9,10,10,10-heptadecafluoro-1-decane-6-thiohexanoic acid

C16H15F17O2S*C6H14N2O2

Conditions
ConditionsYield
In methanol; water for 2h; Reflux;100%
56-87-1

L-lysine

C43H51N7O9S2

(x)C6H14N2O2*C43H51N7O9S2

Conditions
ConditionsYield
In methanol at 20℃; for 4.5h;99.98%
56-87-1

L-lysine

501-53-1

benzyl chloroformate

405-39-0

N,N'-di-[(phenylmethoxy)carbonyl]-L-lysine

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane; water at 20℃; for 1h; pH=10 - 11;99%
With sodium carbonate In diethyl ether; water at 0℃; for 5h;95%
With sodium carbonate In diethyl ether; water at 0℃; for 5h;93%
56-87-1

L-lysine

16611-84-0

6-Pentadecylsalicylic Acid

C6H14N2O2*C22H36O3

Conditions
ConditionsYield
In methanol; water at 10 - 15℃;99%
56-87-1

L-lysine

nicotinic acid riboside 5'-monophosphate

bis((S)-5-amino-5-carboxypentan-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. 6.4 - 6.7;99%
56-87-1

L-lysine

8-(1H,1H,2H,2H-perfluorooctyl)thio-1-octyl succinic acid monoester

C20H25F13O4S*C6H14N2O2

Conditions
ConditionsYield
In methanol for 2h; Reflux;99%
56-87-1

L-lysine

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

C14H9F17O4*C6H14N2O2

Conditions
ConditionsYield
In methanol; water Heating;99%
56-87-1

L-lysine

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

C13H11F13O4*C6H14N2O2

Conditions
ConditionsYield
In methanol; water Heating;99%
56-87-1

L-lysine

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

C15H11F17O4*C6H14N2O2

Conditions
ConditionsYield
In methanol; water Heating;99%
56-87-1

L-lysine

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

C16H9F13O4*C6H14N2O2

Conditions
ConditionsYield
In methanol; water Heating;99%
56-87-1

L-lysine

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

C18H9F17O4*C6H14N2O2

Conditions
ConditionsYield
In methanol; water Heating;99%
56-87-1

L-lysine

53826-12-3

3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctanoic acid

C8H3F13O2*C6H14N2O2

Conditions
ConditionsYield
In methanol; water Heating;99%
56-87-1

L-lysine

36390-05-3

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

2C6H14N2O2*C13H7F17O4

Conditions
ConditionsYield
In methanol; water Heating;99%
56-87-1

L-lysine

36390-05-3

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

C6H14N2O2*C13H7F17O4

Conditions
ConditionsYield
In methanol; water Heating;99%
56-87-1

L-lysine

220072-62-8

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

C14H15F13O2S*C6H14N2O2

Conditions
ConditionsYield
In methanol; water for 2h; Reflux;99%
56-87-1

L-lysine

2-(ginkgolide B-10-oxy)acetic acid

2-(ginkgolide B-10-oxy)acetic acid lysine salt

Conditions
ConditionsYield
In methanol; ethanol at 20℃; for 2h;98.1%
56-87-1

L-lysine

292638-85-8

acrylic acid methyl ester

N,N'-tetrakis(methoxycarbonylethyl)-L-lysine

Conditions
ConditionsYield
In methanol Ambient temperature;98%
Stage #1: L-lysine; acrylic acid methyl ester With sodium hydroxide In methanol Reflux;
Stage #2: With hydrogenchloride In methanol
48.8%
With sodium hydroxide In methanol for 48h; Michael Addition; Heating;48.8%

L-Lysine Specification

 The L-Lysine, with the cas registry number 56-87-1, has the IUPAC name of (2S)-2,6-diaminohexanoic acid. This is a kind of white or almost white crystalline powder with no odour, and it is stable chemically but incompatible with strong oxidizing agents. Besides, its product categories are various, including  Amino Acid Derivatives; Lysine [Lys, K]; Amino Acids; alpha-Amino Acids; Biochemistry; Nutritional Supplements; Amino Acids.

The characteristics of this kind of chemical are as follows: (1)ACD/LogP: -1.04; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -4.54; (4)ACD/LogD (pH 7.4): -4.5; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 4; (10)#H bond donors: 5; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 32.78; (13)Index of Refraction: 1.503; (14)Molar Refractivity: 38.43 cm3; (15)Molar Volume: 129.9 cm3; (16)Polarizability: 15.23×10-24 cm3; (17)Surface Tension: 51.5 dyne/cm; (18)Density: 1.125 g/cm3; (19)Flash Point: 142.2 °C; (20)Enthalpy of Vaporization: 60.75 kJ/mol; (21)Boiling Point: 311.5 °C at 760 mmHg; (22)Vapour Pressure: 0.000123 mmHg at 25°C; (23)Exact Mass: 146.105528; (24)MonoIsotopic Mass: 146.105528; (25)Topological Polar Surface Area: 89.3; (26)Heavy Atom Count: 10; (27)Formal Charge: 0; (28)Complexity: 106.

The production methods of this chemical are as follows: (1) Free L-Lysine could be obtained from L-lysine hydrochloride. (2) Firstly prepare raw material of Red blood cells, and then suspend it  in sulfuric acid solution; Secondly, use the calcium hydroxide to precipitate, and then go through the washing, crystallization to get L-Lysine (CAS NO.56-87-1). (3) Synthesis method: caprolactam and furfural as the raw material.

As to its usage, it is widely applied in many ways. It could be used as the nutrition enhancer which could enhance the lysine in intensified [enriched] food; It could also used in biochemistry  to cure the symptom of malnutrition, inappetence and hypoplasia; And it could be as the Aminoacetic Acid, and the feed additives.

Below are the safety information of this chemical: Being a kind of irritant chemical, it may cause inflammation to the skin or other mucous membranes, so you should avoid contacting with skin and eyes while using.

Additionally, the following datas could be converted into the molecular structure:
(1)Canonical SMILES: C(CCN)CC(C(=O)O)N
(2)Isomeric SMILES: C(CCN)C[C@@H](C(=O)O)N
(3)InChI: InChI=1S/C6H14N2O2/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,10)/t5-/m0/s1
(4)InChIKey: KDXKERNSBIXSRK-YFKPBYRVSA-N 

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