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351-50-8

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351-50-8 Usage

Chemical Properties

white crystalline powder

Uses

D-Histidine is the unnatural, biologically inactive isomer of L-Histidine (H456010). D-histidine is known to inhibit cell division, and is also used by certain types of bacteria (such as Escherichia coli) as a source of L-Histidine.

Definition

ChEBI: An optically active form of histidine having D-configuration.

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.

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.

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.

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