H-His(Trt)-OH
- CAS NO.:35146-32-8
- Empirical Formula: C25H23N3O2
- Molecular Weight: 397.47
- MDL number: MFCD00153444
- EINECS: 609-078-6
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-07-02 08:55:41
What is H-His(Trt)-OH?
Chemical properties
White powder
The Uses of H-His(Trt)-OH
1-(Triphenylmethyl)-L-histidine is a reactant in the synthesis of falcitidin acyl tetrapeptides as antimalarial agent.
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.
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.
Properties of H-His(Trt)-OH
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 |
Safety information for H-His(Trt)-OH
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for H-His(Trt)-OH
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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