35146-32-8

Basic information

• Product Name: H-HIS(TRT)-OH
• Synonyms: 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
• CAS NO: 35146-32-8
• Molecular Formula: C₂₅H₂₃N₃O₂
• Molecular Weight: 397.47
• EINECS: 1308068-626-2
• Product Categories: Histidine [His, H];Amino Acids and Derivatives;Amino Acid Derivatives;Histidine;Peptide Synthesis
• Mol File: 35146-32-8.mol

Chemical Properties

• Melting Point: 210℃
• Boiling Point: 584.8 °C at 760 mmHg
• Flash Point: 307.5 °C
• Appearance: /Solid
• Density: 1.19 g/cm³
• Vapor Pressure: 1.62E-14mmHg at 25°C
• Refractive Index: 1.631
• Storage Temp.: −20°C
• PKA: 1.78±0.10(Predicted)
• CAS DataBase Reference: H-HIS(TRT)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: H-HIS(TRT)-OH(35146-32-8)
• EPA Substance Registry System: H-HIS(TRT)-OH(35146-32-8)

Safety Data

• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 35146-32-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
H-HIS(TRT)-OH is used as a reactant in the synthesis of falcitidin acyl tetrapeptides for its antimalarial properties. These tetrapeptides have demonstrated potential as effective agents against malaria, a widespread and life-threatening disease. The incorporation of H-HIS(TRT)-OH in the synthesis process contributes to the development of new antimalarial drugs, offering alternative treatment options and addressing the challenges of drug resistance in malaria therapy.

InChI:InChI=1/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

Upstream product

• 76-83-5 trityl chloride 
• 71-00-1 L-histidine 
• 71-00-1 L-histidine 
• 109425-51-6 Fmoc-His(Trt)-OH 
• 74853-62-6 N^α,N^im-ditritylhistidine 
• 32946-53-5 N^im-trityl-L-histidine hydrochloride 
• 95383-91-8 L-Histidine 
• 75-78-5 dimethylsilicon dichloride 
• 75-77-4 chloro-trimethyl-silane 

Downstream Products

• 1402572-88-6 PhSNPPOC-histidine(Trt)-OH 
• 1333228-14-0 [{[(S)-1-Methylcarbamoyl-2-(1-trityl-1H-imidazol-4-yl)-ethylcarbamoyl]-methyl}-(3-phenyl-propyl)-amino]-acetic acid methyl ester 
• 1333228-00-4 C₂₆H₂₆N₄O*CH₂O₂ 
• 71-00-1 L-histidine 
• 109425-51-6 Fmoc-His(Trt)-OH 
• 888615-95-0 N^α-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecanoyl)-N^im-(trityl)histidine 
• 362043-68-3 TCP-His(Trt)-OH 
• 82882-72-2 N^α-4-methoxybenzyloxycarbonyl-N^im-tritylhistidine 
• 82882-70-0 N^α-tert-amyloxycarbonyl-N^im-tritylhistidine 

Relevant articles and documents

Preparation method of N - 9 - fluorenylmethoxycarbonyl - N ' - trityl - L - histidine

The invention relates to the technical field of medical intermediate synthesis, in particular to a synthetic method of N - 9 - fluorenylmethoxycarbonyl - N ' - trityl - L - histidine, which comprises the following steps: taking L - histidine as a raw material and protecting a - amino groups on histidine by using a silane protective agent. A silane protecting substance Nim - trityl histidine is obtained by reaction with triphenylchloromethane, followed by addition of water to the silane protecting group. The silane protecting substance Nim - trityl histidine is reacted with 9 - fluorenylmethoxycarbonyl protecting reagent to give the target product N - 9 - fluorenylmethoxycarbonyl - N ' - trityl - L - histidine. The N - 9 -fluorenylmethoxycarbonyl - N ' - trityl - L - histidine preparation method provided by the invention is simple and convenient to operate, high in yield and low in comprehensive production cost, and is suitable for industrial large-scale production.

PYRROLOBENZODIAZEPINE DIMER PRECURSOR AND LIGAND-LINKER CONJUGATE COMPOUND THEREOF

The present invention relates to a pyrrolobenzodiazepine dimer prodrug and a ligand-linker conjugate compound thereof, a composition containing these, and therapeutic use thereof particularly as an anticancer drug. The stability of the compounds themselves and the stability thereof in plasma are excellent and the compounds are advantageous in terms of manifestation of toxicity, and thus the compounds are industrially useful in that it is possible to target proliferative diseases such as cancer, to perform a specific treatment, to maximize the drug efficacy, and to minimize the occurrence of side effects.

Self-healing response in supramolecular polymers based on reversible zinc-histidine interactions

Histidine-metal interactions are utilized in many biological materials as reinforcing crosslinks, and in particular, are believed to contribute as reversible crosslinks to the intrinsic self-recovery behavior of mussel byssal threads. In this contribution

Diverted total synthesis of falcitidin acyl tetrapeptides as new antimalarial leads

We report not only the convergent total synthesis of falcitidin, a natural inhibitor of falcipain-2 from myxobacterium Chitinophaga, but also its diversification into a new antimalarial class of N-acyl tetrapeptides (Acyl-His-Ile-Val-Pro-NH2). Despite the lack of whole-cell activity of falcitidin itself, our study led to the identification of a trifluoromethyl (CF3) analogue displaying sub-micromolar IC50 activity against Plasmodium falciparum 3D7 in a standard blood-cell assay, but only when N-tritylated on its histidine (imidazole) residue.

DIARYLSULPHID BACKBONE CONTAINING PHOTOLABILE PROTECTING GROUPS

The present invention relates to photoactivable protecting groups containing a diarylsulphid chromophore, a method for the synthesis thereof and their use as photoactivable protecting groups using maskless photolithography based array synthesis. wherein R2 is [Formula II] or wherein R2 is [Formula III] or [Formula IV] wherein R7 is a natural amino acid, a non-natural amino acid or an amino acid derivative forming an urethan bond to formula Ib, or wherein formula IV represents the carboxy function of a natural amino acid, a non-natural amino acid or an amino acid derivative, forming an ester bond to formula Ib.

IMPROVED METHODS OF OBTAINING Nim-TRITYL-SUBSTITUTED HISTIDINE DERIVATIVES

Two variants are proposed for the synthesis of Nα-Boc-Nim-tritylhistidiine.The first variant starts from Nα,Nim-di-Boc-histidine, from which the Nim-Boc group is removed with hydrazine hydrate.The Nα-Boc-histidine formed is esterified with chlorotrimethylsilane, tritylated in the imidazole group, and, after the elimination of the trimethylsilyl protection from the carboxyl group, Nα-Boc-Nim-tritylglycine is obtained with a yield of 80percent.The second variant starts from Nα,Nim-ditritylhistidine, which, by treatment with hydrochloric acid in acetone and then with dilute ammonia, is converted into Nim- tritylhistidine.From this, by acylation with di-tert-butyl pyrocarbonate, Nα-Boc-Nim-tritylhistidine is obtained with a yield of 91percent.The acylation of Nim-tritylhistidine with other alkoxycarbonylating reagents leads to Nα-tert-amyl-, Nα-benzyl-, and Nα-4-methoxybenzyloxycarbonyl derivatives of Nim-tritylhistidine.

Efficient "One-Pot" Synthesis of N-Trityl Amino Acids

A sequential procedure has been developed whereby neutral amino acids 1 were tritylated via their corresponding trimethylsilyl esters 2 to afford, after mild hydrolysis, N-trityl amino acids 3 in high yields and purity.Hydroxy amino acids 4 were preferent