74853-62-6

Basic information

• Product Name: TRT-HIS(TRT)-OH
• Synonyms: N-ALPHA,N-IM-DITRITYL-L-HISTIDINE;N-ALPHA,N-TAU-DI-TRITYL-L-HISTIDINE;N-ALPHA-TRITYL-N-IM-TRITYL-L-HISTIDINE;TRT-HIS(TRT)-OH;Nα,Nim-Ditrityl-L-histidine99%
• CAS NO: 74853-62-6
• Molecular Formula: C₄₄H₃₇N₃O₂
• Molecular Weight: 639.78
• Product Categories: Amino Acids
• Mol File: 74853-62-6.mol

Chemical Properties

• Boiling Point: 773.7°C at 760 mmHg
• Flash Point: 421.7°C
• Appearance: /
• Density: 1.13g/cm³
• Vapor Pressure: 3.43E-25mmHg at 25°C
• Refractive Index: 1.626
• Storage Temp.: Store at 0°C
• PKA: 1.62±0.10(Predicted)
• CAS DataBase Reference: TRT-HIS(TRT)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: TRT-HIS(TRT)-OH(74853-62-6)
• EPA Substance Registry System: TRT-HIS(TRT)-OH(74853-62-6)

Safety Data

• Hazardous Substances Data: 74853-62-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Development:
TRT-HIS(TRT)-OH is used as a building block in the synthesis of peptides for various pharmaceutical applications. Its role in creating complex peptide structures is crucial for the development of new drugs and biologically active compounds.
Used in Biochemistry:
In the field of biochemistry, TRT-HIS(TRT)-OH is used as a reagent in solid-phase peptide synthesis. TRT-HIS(TRT)-OH's trityl protecting groups allow for controlled peptide assembly, facilitating the stepwise construction of peptide chains with precise sequences.
Used in Peptide Synthesis:
TRT-HIS(TRT)-OH is used as a protected amino acid in peptide synthesis, ensuring that the histidine residue is incorporated into the peptide chain without unwanted side reactions during the synthesis process. The removal of the TRT protecting groups under acidic conditions allows for the completion of the desired peptide sequence.
Used in the Production of Peptides:
TRT-HIS(TRT)-OH is used as a key component in the production of peptides, which are short chains of amino acids linked by peptide bonds. These peptides have diverse applications in medicine, including as therapeutic agents, diagnostic tools, and research reagents.

InChI:InChI=1/C44H37N3O2/c48-42(49)41(46-43(34-19-7-1-8-20-34,35-21-9-2-10-22-35)36-23-11-3-12-24-36)31-40-32-47(33-45-40)44(37-25-13-4-14-26-37,38-27-15-5-16-28-38)39-29-17-6-18-30-39/h1-30,32-33,41,46H,31H2,(H,48,49)

Upstream product

• 71-00-1 L-histidine 
• 76-83-5 trityl chloride 
• 596-43-0 bromo-triphenyl-methane 
• 645-35-2 L-histidine monohydrochloride 
• 18684-16-7 methyl (2S)-2-amino-3-(1H-imidazol-5-yl)propanoate hydrochloride 
• 75-77-4 chloro-trimethyl-silane 
• 95383-91-8 L-Histidine 
• 121-44-8 triethylamine 
• 1499-46-3 L-Histidine methyl ester 

Downstream Products

• 7763-65-7 (S)-2-[(S)-2-Amino-3-(1H-imidazol-4-yl)-propionylamino]-4-methyl-pentanoic acid 
• 120793-31-9 N-(1,N^α-ditrityl-L-histidyl)-L-phenylalanine-methyl ester 
• 120794-40-3 N-(1,N^α-ditrityl-L-histidyl)=>glycine 
• 97102-81-3 N-formyl-L-alanyl-N(Im)-tosyl-L-histidyl-O-acetyl-D-serine methyl ester 
• 97102-80-2 N-formyl-L-alanyl-N(Im)-tosyl-L-histidyl-O-acetyl-L-serine methyl ester 
• 97102-82-4 N-formyl-D-alanyl-N(Im)-tosyl-L-histidyl-O-acetyl-L-serine methyl ester 
• 97102-83-5 L-carbylalanyl-N(Im)-tosyl-L-histidyl-O-acetyl-D-serine methyl ester 
• 97134-74-2 L-carbylalanyl-N(Im)-tosyl-L-histidyl-O-acetyl-L-serine methyl ester 
• 97134-73-1 D-carbylalanyl-N(Im)-tosyl-L-histidyl-O-acetyl-L-serine methyl ester 
• 120793-36-4 N-(1,N^α-ditrityl-L-histidyl)-L-phenylalanine 
• 35146-32-8 2-amino-3-(N-tritylimidazolyl)propionic acid 
• 32926-43-5 N^α-(tert-butyloxy)carbonyl-N^im-triphenylmethyl-L-histidine 
• 82882-72-2 N^α-4-methoxybenzyloxycarbonyl-N^im-tritylhistidine 
• 82882-71-1 N-α-carboxybenzyl-L-histidine N^im-trityl 

Relevant articles and documents

Synthesis of Polymers of Isocyanides Derived from Tripeptides Containing Imidazolyl, Carboxyl, and Hydroxymethyl Groups

Three optically active polymers of isocyanides, n, which contain imidazolyl, carboxyl, and hydroxymethyl functions in their side chains R, are described.The polymers are derived from the following diastereomeric tripeptides: L-Ala-L-His-L-Ser, L-Ala-L-His-D-Ser, and D-Ala-L-His-L-Ser.The terminal amino groups of these tripeptides are converted into isocyano functions, which are subsequently polymerized with catalytic amounts of nickel(II) chloride.The molecular weights of the polymers are in the Mv range 20000-35000.The CD spectra reveal that the polymers derived from L-Ala-L-His-L-Ser and L-Ala-L-His-D-Ser have right-handed helical configuractions.The pKa values of the imidazolyl and carboxyl groups in the polymers have increased as compared to model compounds.This suggests that strong electrostatic interactions exist between these groups.

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