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

Chemical Properties

White crystalline powder

Uses

It is used in the synthesis and application of Fmoc-His(3-Bum)-OH.

General Description

The product number for this product was previously 04-12-1065.To obtain a certificate of analysis (CoA) of a lot that begins with the letter “A”, please select the option in the right hand menu “Request a COA for Lot#s starting with A”.

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

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

Downstream Products

• 170797-85-0 [(S)-1-[2-(tert-Butyl-dimethyl-silanyloxy)-1,1-bis-(tert-butyl-dimethyl-silanyloxymethyl)-ethylcarbamoyl]-2-(1-trityl-1H-imidazol-4-yl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester 
• 121377-67-1 L-His-L-Leu-L-Asp-L-Ile-L-Ile-L-Trp 
• 192389-07-4 Fmoc-Tyr(t-Bu)-Ile-His(Trt)-Pro-Phe-OH 
• 282529-05-9 methyl 2-(2-{[(9H-fluoren-9-yl)methoxycarbonyl]amino}-3-[1-(triphenylmethyl)-1H-imidazol-4-yl]propanamido)-3-methylbutanoate 
• 276257-16-0 Fmoc-His(Tr)-Ala-Gly-Pro-Ile-NHBn 
• 51274-62-5 [Sar¹,Val⁵]angiotensin II 

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.