1416510-72-9

Basic information

• Product Name: Fmoc-(3,4-DMBom)-OH
• Synonyms: Fmoc-(3,4-DMBom)-OH
• CAS NO: 1416510-72-9
• Molecular Weight: 557.603
• Mol File: 1416510-72-9.mol

Chemical Properties

• CAS DataBase Reference: Fmoc-(3,4-DMBom)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Fmoc-(3,4-DMBom)-OH(1416510-72-9)
• EPA Substance Registry System: Fmoc-(3,4-DMBom)-OH(1416510-72-9)

Safety Data

• Hazardous Substances Data: 1416510-72-9(Hazardous Substances Data)

Upstream product

• 1416510-79-6 C₂₁H₂₉N₃O₇ 
• 1416510-82-1 C₁₆H₂₁N₃O₅ 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 67680-46-0 <(3,4-dimethoxybenzyl)oxy>methyl chloride 
• 17791-52-5 N-(tert-butoxycarbonyl)-L-histidine 

Relevant articles and documents

Synthesis and application of Nα-Fmoc-Nπ-4-methoxybenzyloxymethylhistidine in solid phase peptide synthesis

The 4-methoxybenzyloxymethyl (MBom) group was introduced at the Nπ-position of the histidine (His) residue by using a regioselective procedure, and its utility was examined under standard conditions used for the conventional and the microwave (MW)-assisted solid phase peptide synthesis (SPPS) with 9-fluorenylmethyoxycarbonyl (Fmoc) chemistry. The Nπ-MBom group fulfilling the requirements for the Fmoc strategy was found to prevent side-chain-induced racemization during incorporation of the His residue even in the case of MW-assisted SPPS performed at a high temperature. In particular, the MBom group proved to be a suitable protecting group for the convergent synthesis because it remains attached to the imidazole ring during detachment of the protected His-containing peptide segments from acid-sensitive linkers by treatment with a weak acid such as 1% trifluoroacetic acid in dichloromethane. We also demonstrated the facile synthesis of Fmoc-His(π-MBom)-OH with the aid of purification procedure by crystallization to effectively remove the undesired τ-isomer without resorting to silica gel column chromatography. This means that the present synthetic procedure can be used for large-scale production without any obstacles.