109425-51-6

Basic information

• Product Name: N-Fmoc-N'-trityl-L-histidine
• Synonyms: FMOC-N-IM-TRITYL-L-HISTIDINE;FMOC-HISTIDINE(1-TRT)-OH;FMOC-HIS(TRITYL)-OH;FMOC-HIS(TRT);FMOC-HIS(TRT)-OH;FMOC-HIS(T-TRT)-OH;FMOC-HIS(1-TRT)-OH;FMOC-L-HIS(TRITYL)
• CAS NO: 109425-51-6
• Molecular Formula: C₄₀H₃₃N₃O₄
• Molecular Weight: 619.71
• EINECS: 439-640-4
• Product Categories: Protected Amino Acids;Amino Acid Derivatives;Amino Acids;Histidine [His, H];Fmoc-Amino Acids and Derivatives;Amino Acids (N-Protected);Biochemistry;Fmoc-Amino Acids;Fmoc-Amino acid series
• Mol File: 109425-51-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 150-155 °C(lit.)
• Boiling Point: 811.7 °C at 760 mmHg
• Flash Point: 444.7 °C
• Appearance: White to off-white/Powder
• Density: 1.24 g/cm³
• Vapor Pressure: 7.59E-28mmHg at 25°C
• Refractive Index: 97 ° (C=5, CHCl3)
• Storage Temp.: 2-8°C
• PKA: 3.06±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• Sensitive: Moisture Sensitive
• BRN: 5204720
• CAS DataBase Reference: N-Fmoc-N'-trityl-L-histidine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Fmoc-N'-trityl-L-histidine(109425-51-6)
• EPA Substance Registry System: N-Fmoc-N'-trityl-L-histidine(109425-51-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-24/25
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 109425-51-6(Hazardous Substances Data)

Usage

Description

N-Fmoc-N'-trityl-L-histidine, also known as Fmoc-His(3-Bum)-OH, is a synthetic derivative of the naturally occurring amino acid L-histidine. It is characterized by the presence of two protecting groups: the 9-fluorenylmethoxycarbonyl (Fmoc) group and the trityl (Trt) group. N-Fmoc-N'-trityl-L-histidine is a white crystalline powder and is used in the synthesis and application of Fmoc-His(3-Bum)-OH.

Uses

Used in Peptide Synthesis:
N-Fmoc-N'-trityl-L-histidine is used as a protected amino acid building block for the synthesis of peptides and proteins. The Fmoc group protects the amino group, while the trityl group protects the side chain, allowing for selective deprotection and coupling reactions during solid-phase peptide synthesis.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-Fmoc-N'-trityl-L-histidine is used as an intermediate in the synthesis of various drug candidates and active pharmaceutical ingredients. Its protected structure facilitates the incorporation of L-histidine into complex molecular architectures with controlled selectivity and reactivity.
Used in Research and Development:
N-Fmoc-N'-trityl-L-histidine is also used in research and development for the study of protein structure, function, and interactions. Its protected form allows for the controlled incorporation of L-histidine into peptides and proteins, enabling the investigation of its role in biological systems and the development of novel therapeutic agents.
General Description:
The product number for N-Fmoc-N'-trityl-L-histidine was previously 04-12-1065. To obtain a certificate of analysis (CoA) for a lot that begins with the letter "A", the option "Request a COA for Lot#s starting with A" should be selected in the right-hand menu.

InChI:InChI=1/C40H33N3O4/c44-38(45)37(42-39(46)47-26-36-34-22-12-10-20-32(34)33-21-11-13-23-35(33)36)24-31-25-41-27-43(31)40(28-14-4-1-5-15-28,29-16-6-2-7-17-29)30-18-8-3-9-19-30/h1-23,25,27,36-37H,24,26H2,(H,42,46)(H,44,45)/p-1/t37-/m0/s1

Upstream product

• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 35146-32-8 2-amino-3-(N-tritylimidazolyl)propionic acid 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 

Downstream Products

• 149624-92-0 N⁶-α-(Fluoren-9-ylmethoxycarbonyl)-N_(im)-(triphenylmethyl)-L-histidyl>-6-amino-1-hexanol 
• 149624-96-4 N⁶-α-(Fluoren-9-ylmethoxycarbonyl)-N_(im)-(triphenylmethyl)-L-histidyl>-6-aminohexyl 2-cyanoethyl N,N-diisopropylphosphoramidite 

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.

Efficient procedure for the preparation of oligomer-free N-fmoc amino acids

A two-step method is presented for the peptide-free, high-purity, and high-yield synthesis of N-Fmoc amino acids. The first step involves the preparation of stable dicyclohexylammonium-amino acid ionic adduct in acetone. Subsequently, the ionic adducts, on reaction with Fmoc-Nosu under mild alkaline conditions, give dipeptide-free N-Fmoc amino acids. The positive charge of the dicyclohexylammonium counterion in the ionic salt has a longer radius, moderating the nucleophilicity of the carboxylate ion of the amino acid and preventing by-products by arresting the formation of mixed anhydrides, the precursors of oligopeptide impurities.

Application of the Trt and Fmoc Groups for the Protection of Polyfunctional α-Amino Acids

Simple methods for the preparation of ditrityl amino acids 3 and their application for the synthesis of the peptides 9-27 are described.Selective detritylation of 3 and of the synthesized ditrityl peptides is achieved with 1percent trifluoroacetic acid in dichloromethane.The resulting Nα-detritylated amino acids 5 were converted into the corresponding fluorenylmethoxycarbonyl amino acids 6 under Schotten-Baumann conditions using fluorenylmethyl chloroformate.