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D-Histidine is the unnatural, biologically inactive isomer of L-Histidine (H456010). It is an amino acid that plays a crucial role in various biological processes, including cell division and growth.

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  • 351-50-8 Structure
  • Basic information

    1. Product Name: D-Histidine
    2. Synonyms: H-D-HIS-OH;HISTIDINE, D-;D-ALPHA-AMINO-BETA-IMIDAZOLEPROPIONIC ACID;D-ALPHA-AMINO-BETA-(4-IMIDAZOLYL)PROPIONIC ACID;D-2-AMINO-3-(4-IMIDAZOLYL)PROPIONIC ACID;D-HIS-OH;D-HISTIDINE;D-HIS
    3. CAS NO:351-50-8
    4. Molecular Formula: C6H9N3O2
    5. Molecular Weight: 155.15
    6. EINECS: 206-513-8
    7. Product Categories: Amino Acid Derivatives;Histidine [His, H];Amino Acids and Derivatives;alpha-Amino Acids;Amino Acids;Biochemistry;Amino Acids;amino acid
    8. Mol File: 351-50-8.mol
  • Chemical Properties

    1. Melting Point: 280-290 °C (dec.)
    2. Boiling Point: 278.95°C (rough estimate)
    3. Flash Point: 231.3 °C
    4. Appearance: White/Free-Flowing Powder
    5. Density: 1.3092 (rough estimate)
    6. Vapor Pressure: 3.25E-09mmHg at 25°C
    7. Refractive Index: -13 ° (C=11, 6mol/L HCl)
    8. Storage Temp.: Store at RT.
    9. Solubility: 1 M HCl: soluble
    10. PKA: 1.91±0.10(Predicted)
    11. Water Solubility: 42 g/L (25 ºC)
    12. Merck: 14,4720
    13. BRN: 84089
    14. CAS DataBase Reference: D-Histidine(CAS DataBase Reference)
    15. NIST Chemistry Reference: D-Histidine(351-50-8)
    16. EPA Substance Registry System: D-Histidine(351-50-8)
  • Safety Data

    1. Hazard Codes: Xn
    2. Statements: N/A
    3. Safety Statements: 22-24/25-36/37-26
    4. WGK Germany: 3
    5. RTECS:
    6. TSCA: Yes
    7. HazardClass: N/A
    8. PackingGroup: N/A
    9. Hazardous Substances Data: 351-50-8(Hazardous Substances Data)

351-50-8 Usage

Uses

Used in Pharmaceutical Industry:
D-Histidine is used as an inhibitor of cell division for its ability to interfere with the normal functioning of L-Histidine, which is essential for cell growth and division.
Used in Microbiology:
D-Histidine is used as a source of L-Histidine for certain types of bacteria, such as Escherichia coli. This allows these bacteria to synthesize L-Histidine, which is necessary for their growth and survival.

Biochem/physiol Actions

D-Histidine may be used in the design of peptide drugs, cationic peptides, such as analogues of carnosine. D-Histidine may also be used as a heavy metal sequestration agent.

Check Digit Verification of cas no

The CAS Registry Mumber 351-50-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,5 and 1 respectively; the second part has 2 digits, 5 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 351-50:
(5*3)+(4*5)+(3*1)+(2*5)+(1*0)=48
48 % 10 = 8
So 351-50-8 is a valid CAS Registry Number.
InChI:InChI=1/C6H9N3O2/c7-5(6(10)11)1-4-2-8-3-9-4/h2-3,5H,1,7H2,(H,8,9)(H,10,11)/t5-/m1/s1

351-50-8 Well-known Company Product Price

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

  • (H0998)  D-Histidine  >99.0%(T)(HPLC)

  • 351-50-8

  • 5g

  • 490.00CNY

  • Detail
  • TCI America

  • (H0998)  D-Histidine  >99.0%(T)(HPLC)

  • 351-50-8

  • 25g

  • 1,590.00CNY

  • Detail
  • Alfa Aesar

  • (B21027)  D-Histidine, 99%   

  • 351-50-8

  • 5g

  • 853.0CNY

  • Detail
  • Alfa Aesar

  • (B21027)  D-Histidine, 99%   

  • 351-50-8

  • 25g

  • 2389.0CNY

  • Detail
  • Alfa Aesar

  • (B21027)  D-Histidine, 99%   

  • 351-50-8

  • 100g

  • 7659.0CNY

  • Detail
  • Sigma

  • (H3751)  D-Histidine  ≥98% (TLC)

  • 351-50-8

  • H3751-5G

  • 2,233.53CNY

  • Detail
  • Sigma

  • (H3751)  D-Histidine  ≥98% (TLC)

  • 351-50-8

  • H3751-25G

  • 8,049.60CNY

  • Detail
  • Vetec

  • (V900379)  D-Histidine  Vetec reagent grade, 98%

  • 351-50-8

  • V900379-50G

  • 1,008.54CNY

  • Detail

351-50-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name D-histidine

1.2 Other means of identification

Product number -
Other names D-Histidine

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:351-50-8 SDS

351-50-8Synthetic route

A

L-histidine
71-00-1

L-histidine

B

D-histidin
351-50-8

D-histidin

Conditions
ConditionsYield
durch fraktionierte Krystallisation des d-weinsaeuren Salzes; das Salz des d-Histidins krystallisiert zuerst aus;
D-histidin
351-50-8

D-histidin

Conditions
ConditionsYield
durch gaerende Hefe;
Verfuettern an Kaninchen wird im Harn ausgeschieden;
L-histidine
71-00-1

L-histidine

D-histidin
351-50-8

D-histidin

Conditions
ConditionsYield
With hydrogenchloride; water at 150 - 160℃; Trennung des erhaltenen Racemats ueber das Lg-Tartrat;
D,L-histidine
71-00-1

D,L-histidine

D-histidin
351-50-8

D-histidin

Conditions
ConditionsYield
durch Einw. von gaerender Hefe;
Nα-acetyl-D-histidine
75983-68-5

Nα-acetyl-D-histidine

D-histidin
351-50-8

D-histidin

Conditions
ConditionsYield
With hydrogenchloride; water
D,L-histidine
71-00-1

D,L-histidine

A

L-histidine
71-00-1

L-histidine

B

D-histidin
351-50-8

D-histidin

DL-histidine-hydrochloride

DL-histidine-hydrochloride

D-histidin
351-50-8

D-histidin

Conditions
ConditionsYield
With water Produkt ist Hydrochlorid;
With L-amino acid oxide ase from the toxin of crotalus adamanteus
d-tartrate from dl-histidine

d-tartrate from dl-histidine

D-histidin
351-50-8

D-histidin

Conditions
ConditionsYield
With water fraktionierte Krystallisation;
N-acetylhistidine
10101-30-1

N-acetylhistidine

D-histidin
351-50-8

D-histidin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: enzymesubstance from pig's kidney
2: water; HCl
View Scheme
(PPh3)2 PdCl2

(PPh3)2 PdCl2

1-acetamido-2-(4-imidazolyl)ethene

1-acetamido-2-(4-imidazolyl)ethene

D-histidin
351-50-8

D-histidin

Conditions
ConditionsYield
With CO In tetrahydrofuran; hydrogenchloride
1-acetamido-2-(4-imidazolyl)ethene

1-acetamido-2-(4-imidazolyl)ethene

D-histidin
351-50-8

D-histidin

Conditions
ConditionsYield
With CO; (PPh3)2PdCl2 In tetrahydrofuran; hydrogenchloride
D-histidin
351-50-8

D-histidin

Conditions
ConditionsYield
With Streptomyces spp. 83D12 D-aminopeptidase In dimethyl sulfoxide at 20℃; for 0.0833333h; pH=6.5; aq. buffer; Enzymatic reaction;
(S)-1-((S)-2-((2S,3S)-2-((R)-3-(1H-imidazol-4-yl)-2-(3-methylbutanamido)-propanamido)-3-methylpentanamido)-3-methylbutanoyl)pyrrolidine-2-carboxamide formate salt

(S)-1-((S)-2-((2S,3S)-2-((R)-3-(1H-imidazol-4-yl)-2-(3-methylbutanamido)-propanamido)-3-methylpentanamido)-3-methylbutanoyl)pyrrolidine-2-carboxamide formate salt

A

L-valine
72-18-4

L-valine

B

L-isoleucine
73-32-5

L-isoleucine

C

L-proline
147-85-3

L-proline

D

D-histidin
351-50-8

D-histidin

Conditions
ConditionsYield
With hydrogenchloride In water at 170℃; for 0.333333h; Microwave irradiation;
D-histidin
351-50-8

D-histidin

norcantharidin
29745-04-8

norcantharidin

D-histidine norcantharimide

D-histidine norcantharimide

Conditions
ConditionsYield
In ethanol; water for 48h; Reflux;95%
D-histidin
351-50-8

D-histidin

(S)-4,4-dimethyl-5-methyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridinyl-6-carboxylic acid dihydrochloride

(S)-4,4-dimethyl-5-methyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridinyl-6-carboxylic acid dihydrochloride

Conditions
ConditionsYield
With formaldehyd; palladium dihydroxide In water; hydrogen94.5%
C32H28N2O4

C32H28N2O4

D-histidin
351-50-8

D-histidin

C38H35N5O5

C38H35N5O5

Conditions
ConditionsYield
In methanol for 48h; Inert atmosphere;92%
methanol
67-56-1

methanol

D-histidin
351-50-8

D-histidin

Methyl (2R)-2-chloro-3-(1H-imidazol-4-yl)propanoate
70240-70-9

Methyl (2R)-2-chloro-3-(1H-imidazol-4-yl)propanoate

Conditions
ConditionsYield
Stage #1: D-histidin With hydrogenchloride; sodium nitrite
Stage #2: methanol With hydrogenchloride Fischer esterification; Reflux;
90%
formaldehyd
50-00-0

formaldehyd

4-(1,2,3-selenadiazol-4-yl)-[1,2,4]triazolo[1,5-a]quinoline-2,8-diol

4-(1,2,3-selenadiazol-4-yl)-[1,2,4]triazolo[1,5-a]quinoline-2,8-diol

D-histidin
351-50-8

D-histidin

2-((2,8-dihydroxy-4-(1,2,3-selenadiazol-4-yl)-[1,2,4]triazolo[1,5-a]quinolin-9-yl)methylamino)-3-(1H-imidazol-4-yl)propanoic acid

2-((2,8-dihydroxy-4-(1,2,3-selenadiazol-4-yl)-[1,2,4]triazolo[1,5-a]quinolin-9-yl)methylamino)-3-(1H-imidazol-4-yl)propanoic acid

Conditions
ConditionsYield
With triethylamine In ethanol at 60℃;71%
1,3,5-benzene tris(carbonyl chloride)
4422-95-1

1,3,5-benzene tris(carbonyl chloride)

D-histidin
351-50-8

D-histidin

2-[4,6-bis[(1-carboxy-2-imidazolyl)ethylcarbamoyl]benzenecarbonyl]amino-3-imidazolylpropionic acid

2-[4,6-bis[(1-carboxy-2-imidazolyl)ethylcarbamoyl]benzenecarbonyl]amino-3-imidazolylpropionic acid

Conditions
ConditionsYield
Stage #1: D-histidin With potassium hydroxide In tetrahydrofuran at 0℃;
Stage #2: 1,3,5-benzene tris(carbonyl chloride) With potassium hydroxide In tetrahydrofuran at 0 - 20℃;
67%
formaldehyd
50-00-0

formaldehyd

1-(2,8-dihydroxy-[1,2,4]triazolo[1,5-a]quinolin-4-yl)ethanone

1-(2,8-dihydroxy-[1,2,4]triazolo[1,5-a]quinolin-4-yl)ethanone

D-histidin
351-50-8

D-histidin

2-((2,8-dihydroxy-4-acetyl-[1,2,4]triazolo[1,5-a]quinolin-9-yl)methylamino)-3-(1H-imidazol-4-yl)propanoic acid

2-((2,8-dihydroxy-4-acetyl-[1,2,4]triazolo[1,5-a]quinolin-9-yl)methylamino)-3-(1H-imidazol-4-yl)propanoic acid

Conditions
ConditionsYield
With triethylamine In ethanol at 60℃;64%
2-Picolinic acid
98-98-6

2-Picolinic acid

nickel(II) chloride hexahydrate

nickel(II) chloride hexahydrate

D-histidin
351-50-8

D-histidin

C12H14N4NiO5

C12H14N4NiO5

Conditions
ConditionsYield
Stage #1: 2-Picolinic acid; nickel(II) chloride hexahydrate In methanol; water
Stage #2: D-histidin With potassium hydroxide In methanol; water at 20℃; for 2h;
63%
D-histidin
351-50-8

D-histidin

3-formyl-9-hexylcarbazole
183718-72-1

3-formyl-9-hexylcarbazole

C25H30N4O2

C25H30N4O2

Conditions
ConditionsYield
Stage #1: D-histidin; 3-formyl-9-hexylcarbazole With lithium hydroxide monohydrate In methanol at 80℃; for 12h;
Stage #2: With sodium tetrahydroborate In methanol at 20℃;
62%
2-Picolinic acid
98-98-6

2-Picolinic acid

copper(II) choride dihydrate

copper(II) choride dihydrate

D-histidin
351-50-8

D-histidin

C12H14CuN4O5

C12H14CuN4O5

Conditions
ConditionsYield
Stage #1: 2-Picolinic acid; copper(II) choride dihydrate In methanol; water
Stage #2: D-histidin With potassium hydroxide In methanol; water at 20℃; for 2h;
61%
Dodecanal
112-54-9

Dodecanal

D-histidin
351-50-8

D-histidin

(4S,6R)-4-undecyl-4,5,6,7-tetrahydro-1H-imidazo-[4,5-c]pyridine-6-carboxylic acid

(4S,6R)-4-undecyl-4,5,6,7-tetrahydro-1H-imidazo-[4,5-c]pyridine-6-carboxylic acid

Conditions
ConditionsYield
With sodium hydroxide In methanol; water at 25℃; for 0.666667h; Pictet-Spengler Synthesis;49.8%
acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

D-histidin
351-50-8

D-histidin

D-histidine t-butyl ester

D-histidine t-butyl ester

Conditions
ConditionsYield
With perchloric acid In water at 20℃;48.4%
water
7732-18-5

water

nitric acid
7697-37-2

nitric acid

silver nitrate

silver nitrate

L-histidine
71-00-1

L-histidine

D-histidin
351-50-8

D-histidin

[Ag2(L-histidinium)(D-histidinium)(NO3)4]n

[Ag2(L-histidinium)(D-histidinium)(NO3)4]n

Conditions
ConditionsYield
for 72h; pH=3 - 4; Darkness;44%
acetic anhydride
108-24-7

acetic anhydride

D-histidin
351-50-8

D-histidin

Nα-acetyl-D-histidine
75983-68-5

Nα-acetyl-D-histidine

Conditions
ConditionsYield
With acetic acid
D-histidin
351-50-8

D-histidin

(R)-2-hydroxy-3-(1(3)H-imidazol-4-yl)-propionic acid
1141479-01-7

(R)-2-hydroxy-3-(1(3)H-imidazol-4-yl)-propionic acid

Conditions
ConditionsYield
With hydrogenchloride; silver nitrate
D-histidin
351-50-8

D-histidin

R-(+)-4-(2-Amino-3-hydroxypropyl)-imidazol
70142-15-3

R-(+)-4-(2-Amino-3-hydroxypropyl)-imidazol

Conditions
ConditionsYield
/BRN= 81955/;
bufotalin 3-hemisuberate p-nitrophenyl ester
61507-75-3

bufotalin 3-hemisuberate p-nitrophenyl ester

D-histidin
351-50-8

D-histidin

bufotalin 3-suberoyl-D-histidine ester
90052-06-5, 97428-96-1

bufotalin 3-suberoyl-D-histidine ester

Conditions
ConditionsYield
In pyridine; water for 12h; Ambient temperature;8 mg

351-50-8Relevant articles and documents

Preparation and characterization of a new open-tubular capillary column for enantioseparation by capillary electrochromatography

Li, Yingjie,Tang, Yimin,Qin, Shili,Li, Xue,Dai, Qiang,Gao, Lidi

, p. 283 - 292 (2019/02/05)

In order to use the enantioseparation capability of cationic cyclodextrin and to combine the advantages of capillary electrochromatography (CEC) with open-tubular (OT) column, in this study, a new OT-CEC, coated with cationic cyclodextrin (1-allylimidazolium-β-cyclodextrin [AI-β-CD]) as chiral stationary phase (CSP), was prepared and applied for enantioseparation. Synthesized AI-β-CD was characterized by infrared (IR) spectrometry and mass spectrometry (MS). The preparation conditions for the AI-β-CD-coated column were optimized with the orthogonal experiment design L9(34). The column prepared was characterized by scanning electron microscopy (SEM) and elemental analysis (EA). The results showed that the thickness of stationary phase in the inner surface of the AI-β-CD-coated columns was about 0.2 to 0.5?μm. The AI-β-CD content in stationary phase based on the EA was approximately 2.77?mmol·m?2. The AI-β-CD-coated columns could separate all 14 chiral compounds (histidine, lysine, arginine, glutamate, aspartic acid, cysteine, serine, valine, isoleucine, phenylalanine, salbutamol, atenolol, ibuprofen, and napropamide) successfully in the study and exhibit excellent reproducibility and stability. We propose that the column, coated with AI-β-CD, has a great potential for enantioseparation in OT-CEC.

Chromatographic Resolution of α-Amino Acids by (R)-(3,3'-Halogen Substituted-1,1'-binaphthyl)-20-crown-6 Stationary Phase in HPLC

Wu, Peng,Wu, Yuping,Zhang, Junhui,Lu, Zhenyu,Zhang, Mei,Chen, Xuexian,Yuan, Liming

supporting information, p. 1037 - 1042 (2017/07/25)

Three new chiral stationary phases (CSPs) for high-performance liquid chromatography were prepared from R-(3,3'-halogen substituted-1,1'-binaphthyl)-20-crown-6 (halogen = Cl, Br and I). The experimental results showed that R-(3,3'-dibromo-1,1'-binaphthyl)-20-crown-6 (CSP-1) possesses more prominent enantioselectivity than the two other halogen-substituted crown ether derivatives. All twenty-one α-amino acids have different degrees of separation on R-(3,3'-dibromo-1,1'-binaphthyl)-20-crown-6-based CSP-1 at room temperature. The enantioselectivity of CSP-1 is also better than those of some commercial R-(1,1'-binaphthyl)-20-crown-6 derivatives. Both the separation factors (α) and the resolution (Rs) are better than those of commercial crown ether-based CSPs [CROWNPAK CR(+) from Daicel] under the same conditions for asparagine, threonine, proline, arginine, serine, histidine and valine, which cannot be separated by commercial CR(+). This study proves the commercial usefulness of the R-(3,3'-dibromo-1,1'-binaphthyl)-20-crown-6 chiral stationary phase.

An easy 'Filter-and-Separate' method for enantioselective separation and chiral sensing of substrates using a biomimetic homochiral polymer

Senthilkumar,Asha

supporting information, p. 8931 - 8934 (2015/05/27)

We present a polyfluorene appended with protected l-glutamic acid that exhibited a reversible α-helix/β-sheet-like conformation and helical porous fibrous morphology mimicking the super-structure of proteins. The new homochiral polymer probe enabled efficient heterogeneous enantioselective separation and chiral sensing of a wide variety of substrates from their aqueous racemic mixture using an easy 'Filter-and-Separate' method.

SEPARATING AGENT AND MANUFACTURING METHOD THEREOF

-

Paragraph 0067; 0068; 0069; 0070; 0071; 0072; 0073; 0074, (2015/01/07)

An embodiment of the present invention is a separating agent wherein a group represented by a chemical formula of: or a group represented by a chemical formula of: is introduced on a surface thereof.

SEPARATING AGENT FOR CHROMATOGRAPHY

-

Paragraph 0074; 0075, (2013/08/15)

A separating agent for chromatography is provided that is useful for the separation of specific compounds, e.g., for the optical resolution of amino acids. This separating agent for chromatography provides a higher productivity and contains a crown ether-like cyclic structure and optically active binaphthyl. This separating agent for chromatography containing a crown ether-like cyclic structure and optically active binaphthyl is provided by introducing a substitution group for binding to carrier into a specific commercially available 1,1′-binaphthyl derivative that has substituents at the 2, 2′, 3, and 3′ positions, then introducing a crown ether-like cyclic structure, and subsequently chemically bonding the binaphthyl derivative to the carrier through the substitution group for binding to carrier.

Isolation and synthesis of falcitidin, a novel myxobacterial-derived acyltetrapeptide with activity against the malaria target falcipain-2

Somanadhan, Brinda,Kotturi, Santosh R.,Yan Leong, Chung,Glover, Robert P.,Huang, Yicun,Flotow, Horst,Buss, Antony D.,Lear, Martin J.,Butler, Mark S.

, p. 259 - 264 (2013/07/27)

A 384-well microtitre plate fluorescence cleavage assay was developed to identify inhibitors of the cysteine protease falcipain-2, an important antimalarial drug target. Bioassay-guided isolation of a MeOH extract from a myxobacterium Chitinophaga sp. Y23 isolated from soil collected in Singapore, led to the identification of a new acyltetrapeptide, falcitidin (1), which displayed an IC 50 value of 6 μM against falcipain-2. The planar structure of 1 was secured by NMR and MS/MS analysis. Attempts to isolate further material for biological testing were hampered by inconsistent production and by a low yield (100 μg l -1). The absolute configuration of 1 was determined by Marfey's analysis and the structure was confirmed through total synthesis as isovaleric acid-D-His-L-Ile-L-Val-L-Pro-NH 2. Falcitidin (1) is the first member of a new class of falcipain-2 inhibitors and, unlike other peptide-based inhibitors, does not contain reactive groups that irreversibly bind to active cysteine sites.

Aminolytic reaction catalyzed by d-stereospecific amidohydrolases from Streptomyces spp

Arima, Jiro,Ito, Hitomi,Hatanaka, Tadashi,Mori, Nobuhiro

experimental part, p. 1460 - 1469 (2012/01/12)

From investigation of 2000 soil isolates, we identified two serine-type amidohydrolases that can hydrolyze d-aminoacyl derivatives from the culture supernatant of Streptomyces species 82F2 and 83D12. The enzymes, redesignated as 82F2-DAP and 83D12-DAP, were purified for homogeneity and characterized. Each enzyme had molecular mass of approximately 40 kDa, and each showed moderate stability with respect to temperature and pH. Among hydrolytic activities toward d-aminoacyl-pNAs, the enzymes showed strict specificity toward d-Phe-pNA, but showed broad specificity toward d-aminoacyl esters. The specific activity for d-Phe-pNA hydrolysis of 82F2-DAP was ten-fold higher than that of 83D12-DAP. As a second function, each enzyme showed peptide bond formation activity by its function of aminolysis reaction. Based on results of d-Phe-d-Phe synthesis under various conditions, we propose a reaction mechanism for d-Phe-d-Phe production. Furthermore, the enzymes exhibited peptide elongation activity, producing oligo homopeptide in a one-pot reaction. We cloned the genes encoding each enzyme, which revealed that the primary structure of each enzyme showed 30-60% identity with those of peptidases belonging to the clan SE, S12 peptidase family categorized as serine peptidase with d-stereospecificity.

Amino acid ionic liquids as chiral ligands in ligand-exchange chiral separations

Liu, Qian,Wu, Kangkang,Tang, Fei,Yao, Lihua,Yang, Fei,Nie, Zhou,Yao, Shouzhuo

body text, p. 9889 - 9896 (2010/04/06)

Recently, amino acid ionic liquids (AAILs) have attracted much research interest. In this paper, we present the first application of AAILs in chiral separation based on the chiral ligand exchange principle. By using 1alkyl-3-methylimidazolium L-proline (L-Pro) as a chiral ligand coordinated with copper(II), four pairs of underivatized amino acid enantiomers - DLphenylalanine (DL-Phe), DL-histidine (DL-His), DL-tryptophane (DL-Trp), and DL-tyrosine (DL-Tyr) - were successfully separated in two major chiral separation techniques, HPLC and capillary electrophoresis (CE), with higher enantioselectivity than conventionally used amino acid ligands (resolution (Rs) = 3.26-10.81 for HPLC; Rs = 1.34-4.27 for CE). Interestingly, increasing the alkyl chain length of the AAIL cation remarkably enhanced the enantioselectivity. It was inferred that the alkylmethylimidazolium cations and L-Pro form ion pairs on the surface of the sta-tionary phase or on the inner surface of the capillary. The ternary copper complexes with L-Pro are consequently attached to the support surface, thus inducing an ion-exchange type of retention for the DL-enantiomers. Therefore, the AAIL cation plays an essential role in the separation. This work demonstrates that AAILs are good alternatives to conventional amino acid ligands for ligand-exchange-based chiral separation. It also reveals the tremendous application potential of this new type of task-specific ILs.

Chiral separation of underivatized amino acids by reactive extraction with palladium-BINAP complexes

Verkuijl, Bastiaan J. V.,Minnaard, Adriaan J.,De Vries, Johannes G.,Feringa, Ben L.

experimental part, p. 6526 - 6533 (2010/03/01)

(Figure Presented) In answer to the need for a more economic technology for the separation of racemates, a novel system for reactive enantioselective liquid-liquid extraction (ELLE) is introduced. Palladium (S)-BINAP complexes are employed as hosts in the separation of underivatized amino acids. The system shows the highest selectivity for the ELLE of tryptophan with metal complexes as hosts reported to date and shows a good selectivity toward a range of natural and unnatural amino acids. Furthermore, the host can be prepared in situ from commerically available compounds. Bulk-membrane transport in the form of U-tube experiments demonstrates the enantioselective and catalytic nature of the transport. The dependency of the system on parameters such as pH, organic solvent, and host-substrate ratio has been established. 31P NMR spectroscopy has been used to confirm the preferred enantiomer in the extraction experiments. The intrinsic selectivity was deduced by determination of the association constants of the palladium complex with the tryptophan enantiomers.

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