112380-10-6

Basic information

• Product Name: FMOC-HIS(TOS)-OH
• Synonyms: FMOC-N-IM-4-TOLUENESYLFONYL-L-HISTIDINE;FMOC-HIS(TOS)-OH;FMOC-HIS(TOS)-OH 98+%;nα-fmoc-n(im)-tosyl-l-histidine;(S)-2-((((9H-Fluoren-9-yl)Methoxy)carbonyl)aMino)-3-(1-tosyl-1H-iMidazol-4-yl)propanoic acid;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-1-[(4-methylphenyl)sulfonyl]-L-histidine;Nalpha-Fmoc-Nim-4-toluenesylfonyl-L-histidine;Fmoc-L-His(Tos)-OH
• CAS NO: 112380-10-6
• Molecular Formula: C₂₈H₂₅N₃O₆S
• Molecular Weight: 531.58
• Mol File: 112380-10-6.mol
• Article Data: 1

Chemical Properties

• Melting Point: 170-174 °C (dec.)
• Appearance: /
• Density: 1.4 g/cm³
• Refractive Index: 1.677
• Storage Temp.: 2-8°C
• PKA: 3.39±0.10(Predicted)
• CAS DataBase Reference: FMOC-HIS(TOS)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-HIS(TOS)-OH(112380-10-6)
• EPA Substance Registry System: FMOC-HIS(TOS)-OH(112380-10-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 112380-10-6(Hazardous Substances Data)

Usage

General Description

FMOC-HIS(TOS)-OH, or Fmoc-Histidine Tosylate, is a chemical compound often utilized in peptide synthesis. This organic compound belongs to the class of protected amino acids, where FMOC (9-Fluorenylmethoxycarbonyl) is a protective group for the amino part and HIS represents Histidine, an essential amino acid. TOS (Tosylate) acts as a protective group for the imidazole side chain in histidine. The OH indicates the presence of a hydroxyl group. The key purpose of this compound is to facilitate high-efficiency peptide coupling without unwanted side reactions during solid-phase peptide synthesis. The tosylate counterion enhances the solubility of this compound in commonly used solvents. FMOC-HIS(TOS)-OH is particularly valuable in pharmaceutical research and development, especially concerning drug discovery and development.

InChI:InChI=1/C28H25N3O6S/c1-18-10-12-20(13-11-18)38(35,36)31-15-19(29-17-31)14-26(27(32)33)30-28(34)37-16-25-23-8-4-2-6-21(23)22-7-3-5-9-24(22)25/h2-13,15,17,25-26H,14,16H2,1H3,(H,30,34)(H,32,33)/t26-/m0/s1

Upstream product

• 116611-64-4 (9-fluorenylmethoxycarbonyl)-L-histidine 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 83345-50-0 Fmoc-His(Tos) anhydride 

Relevant articles and documents

Alpha-N-methylhistidine intermediate and preparation method thereof

The invention relates to an alpha-N-methylhistidine intermediate and a preparation method thereof. The intermediate has a chemical structure as shown in a formula I, wherein R is selected from the group consisting of methyl, phenyl, p-methylphenyl, o-methylphenyl, meta-methylphenyl, 2,4-dimethylphenyl, 2-nitrophenyl, 4-nitrophenyl, 2,4-dinitrophenyl, p-methoxyphenyl, 2,4-dimethoxyphenyl or benzyl; and PG is a protection group. The alpha-N-methylhistidine intermediate can successfully realize subsequent chemical reactions and obtain N-methylhistidine with extremely-high optical purity; meanwhile, subsequent protection groups are easy to be removed, and decomposition of products and damage of optical purity may not be caused; and more importantly, the preparation method for the alpha-N-methylhistidine intermediate is simple and solves problems of difficult production and incapable mass production of alpha-N-methylhistidine in the prior art.