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H-His(Trt)-OH

Product Name
H-His(Trt)-OH
CAS No.
35146-32-8
Chemical Name
H-His(Trt)-OH
Synonyms
His(Trt);L-His(Trt);L-His(Trt)-OH;H-HIS(TRT)-OH;L-His(Trt)·H2O;H-L-HIS(TRT)-OH;H-HIS(T-TRT)-OH;H-HIS(1-TRT)-OH;H-His(tau-Trt)-OH;HISTIDINE(1-TRT)-OH
CBNumber
CB9185713
Molecular Formula
C25H23N3O2
Formula Weight
397.47
MOL File
35146-32-8.mol
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H-His(Trt)-OH Property

Melting point:
210℃
Boiling point:
584.8±50.0 °C(Predicted)
Density 
1.19±0.1 g/cm3(Predicted)
storage temp. 
Sealed in dry,Store in freezer, under -20°C
pka
1.78±0.10(Predicted)
form 
Solid
color 
White to off-white
InChI
InChI=1S/C25H23N3O2/c26-23(24(29)30)16-22-17-28(18-27-22)25(19-10-4-1-5-11-19,20-12-6-2-7-13-20)21-14-8-3-9-15-21/h1-15,17-18,23H,16,26H2,(H,29,30)/t23-/m0/s1
InChIKey
BSZQZNOAYQCQFZ-QHCPKHFHSA-N
SMILES
C(O)(=O)[C@H](CC1N=CN(C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=1)N
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Safety

WGK Germany 
3
F 
10
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

TRC
Product number
T808775
Product name
1-(Triphenylmethyl)-L-histidine
Packaging
10g
Price
$120
Updated
2021/12/16
Usbiological
Product number
285606
Product name
Nim-Trityl-histidine
Packaging
2g
Price
$333
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
AAA0002849
Product name
H-HIS(TRT)-OH
Purity
95.00%
Packaging
1G
Price
$151.83
Updated
2021/12/16
ChemScene
Product number
CS-W013871
Product name
H-His(Trt)-OH
Purity
99.41%
Packaging
25g
Price
$120
Updated
2021/12/16
Activate Scientific
Product number
AS102790
Product name
H-His(Trt)-OH
Purity
97%
Packaging
1g
Price
$23
Updated
2021/12/16
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H-His(Trt)-OH Chemical Properties,Usage,Production

Chemical Properties

White powder

Uses

1-(Triphenylmethyl)-L-histidine is a reactant in the synthesis of falcitidin acyl tetrapeptides as antimalarial agent.

Preparation

The amino acid N(im)-trityl-D-histidine was dissolved in dichloromethane, followed by the addition of triethylamine and trimethylsilyl chloride (3.5 equivalents). After 2 hours of gentle reflux, the mixture was ready to be used for in situ coupling to the anhydride of the carboxylic acid. Thus, isovaleric acid was separately dissolved in THF and maintained at -20 ℃ using an ice-salt bath. N-methyl morpholine (1.2 equivalents) was added, followed by the addition of ethyl chloroformate (1.0 equivalent). After 15-20 minutes at -20 ℃, the bis-TMS amino acid reaction mixture was added directly to the anhydride solution and left stirring at room temperature overnight. After 8 hours, the reaction mixture was concentrated in vacuo. Finally, H-His(Trt)-OH was obtained after purification.

Definition

H-His(Trt)-OH, also known as 1-(Triphenylmethyl)-L-histidine, is a histidine derivative. It can be obtained by removing fmoc group protection from Fmoc-His(Trt)-OH. L-histidine (HIS) is an essential amino acid with unique roles in proton buffering, metal ion chelation, scavenging of reactive oxygen and nitrogen species, erythropoiesis, and the histaminergic system.

Synthesis

109425-51-6

35146-32-8

General procedure for the synthesis of N'-(triphenylmethyl)-L-histidine from N-Fmoc-N'-trityl-L-histidine: Fmoc-His(Trt)-OH (100 g, 0.161 mol, 1 eq.) was dissolved in THF (2000 mL) and piperidine (140 g, 1.614 mol, 10 eq.) was added under stirring conditions. The reaction mixture was stirred for 2 hours using a mechanical stirrer. The progress of the reaction was monitored by thin layer chromatography (TLC) to confirm the complete removal of the Fmoc protecting group. Subsequently, water (~4 L) was added to the reaction system and stirring was continued for 30 min. The precipitate was collected by filtration. The filtrate was concentrated to remove THF completely. pH of the solution was adjusted to 2.5 with dilute hydrochloric acid and the mixture was stirred overnight. Filtration yielded 53 g of colorless crystals (83% yield) and the product was dried in air overnight.

References

[1] Patent: WO2012/136604, 2012, A1. Location in patent: Page/Page column 42-43
[2] Tetrahedron Letters, 2014, vol. 55, # 11, p. 1949 - 1951

H-His(Trt)-OH Preparation Products And Raw materials

Raw materials

Preparation Products

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H-His(Trt)-OH Suppliers

China 179 France 1 Germany 4 Hungary 1 India 2 Japan 2 South Korea 1 Switzerland 2 United Kingdom 1 United States 15 Global 208
Reanal Finechemical Private Ltd.
Tel
--
Fax
--
Email
sales@reanal.hu
Country
Hungary
ProdList
132
Advantage
50
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View Lastest Price from H-His(Trt)-OH manufacturers

Sichuan HongRi Pharma-Tech Co.,Ltd
Product
H-L-His(trt)-OH 35146-32-8
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
98%;99%
Supply Ability
1T+
Release date
2023-09-08
Sichuan Jiaying Lai Technology Co.,LTD
Product
H-His(trt)-OH 35146-32-8
Price
US $1.00/g
Min. Order
1g
Purity
98%
Supply Ability
100KG
Release date
2019-07-25
Career Henan Chemical Co
Product
H-HIS(TRT)-OH 35146-32-8
Price
US $1.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
1kg,5kg,100kg
Release date
2019-07-04

35146-32-8, H-His(Trt)-OHRelated Search:

Methyl L-histidinate dihydrochloride H-HIS(BZL)-OH 3-METHYL-L-HISTIDINE H-His(Trt)-OMe · HCl 3,5-DIIODO-D-TYROSINE HYDROCHLORIDE Fmoc-His(Trt)-OH N-Fmoc-N'-Trityl-L-histidine pentafluorophenyl ester H-His(Trt)-OH Boc-His(Trt)-OH TRT-OH N-Boc-S-Trityl-L-cysteine N-Boc-N'-trityl-L-glutamine N-FMOC-GLY(TRT)-OH Z-GLN(TRT)-OH,Z-GLUTAMINE(TRT)-OH FMOC-D-PEN(TRT)-OH Z-ASN(TRT)-OH Fmoc-Asn(Trt)-OH H-GLN(TRT)-OH

  • N-τ-Trityl-L-histidine
  • 1-(Triphenylmethyl)-L-histidine
  • L-His(Trt)·H2O
  • L-His(Trt)-OH
  • Nim-Trityl-histidine≥ 98% (HPLC)
  • (2S)-2-amino-3-(1-tritylimidazol-4-yl)propanoicacid
  • 1-Trityl-L-histidine, 98%
  • H-L-HIS(TRT)-OH
  • HISTIDINE(1-TRT)-OH
  • H-HIS(1-TRT)-OH
  • H-HIS(T-TRT)-OH
  • H-HIS(TRT)-OH
  • RARECHEM AL BE 1480
  • N-IM-TRITYL-HISTIDINE
  • N-IM-TRITYL-L-HISTIDINE
  • N-TAU-TRITYL-L-HISTIDINE
  • His(Trt)
  • N<T/(IM)>-TRITYL-L-HISTIDINE
  • H-His(tau-Trt)-OH
  • (2S)-2-amino-3-[1-(triphenylmethyl)-1H-imidazol-4-yl]propanoic acid
  • (2S)-2-amino-3-[1-(triphenylmethyl)-4-imidazolyl]propanoic acid
  • L-His(Trt)
  • (2S)-2-ammonio-3-(1-trityl-1H-imidazol-4-yl)propanoate
  • (S)-2-Amino-3-(1-trityl-1H-imidazol-4-yl)propanoicacid
  • L-Histidine, 1-(triphenylmethyl)-
  • (2S)-2-amino-3-(1-tritylimidazol-4-yl)propanoicaci
  • H-HIS(TRT)-OH USP/EP/BP
  • 1-Trityl-L-histidine, 98%
  • 35146-32-8
  • C25H23N3O2
  • Histidine
  • Peptide Synthesis
  • Specialty Synthesis
  • Amino Acid Derivatives
  • Histidine [His, H]
  • Amino Acids and Derivatives
  • Amino Acid Derivatives
  • Histidine
  • Peptide Synthesis