17791-51-4

Basic information

• Product Name: N(ALPHA) N-(IM)-DI-BOC-L-HISTIDINE
• Synonyms: Na,N-(im)-Di-BOC-L-histidinemethylester;[methyl(s)-3[1-(1,1-dimethylethoxycarbonyl)-1-h-imidaral-4-yl]-2-[(1,1-dimethylethoxycarbonyl)amino]propionate];n(α), n-(im)-di-boc-l-histidine methyl ester;[Methyl(S)-3[1-(1,1-dimethylethoxycarbonyl)-1-H-imidazol-4-yl]-2-[(1,1-dimethylethoxycarbonyl)amino]propionate];N(alpha), N-(im)-Di-Boc-L-histidine methyl ester 97%;Boc-L-His(Boc)-OMe;Nα,Nim-Bis-Boc-L-histidine methyl ester99%;(Tert-Butoxy)Carbonyl His(Boc)-OMe
• CAS NO: 17791-51-4
• Molecular Formula: C17H27N3O6
• Molecular Weight: 369.415
• Mol File: 17791-51-4.mol
• Article Data: 8

Chemical Properties

• Melting Point: 113-116 °C(lit.)
• Appearance: /
• Density: 1.17g/cm3
• Refractive Index: 1.516
• Storage Temp.: Store at 0-5°C
• CAS DataBase Reference: N(ALPHA) N-(IM)-DI-BOC-L-HISTIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: N(ALPHA) N-(IM)-DI-BOC-L-HISTIDINE(17791-51-4)
• EPA Substance Registry System: N(ALPHA) N-(IM)-DI-BOC-L-HISTIDINE(17791-51-4)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 17791-51-4(Hazardous Substances Data)

Usage

General Description

N(ALPHA) N-(IM)-DI-BOC-L-HISTIDINE is a compound used in organic chemistry and biochemistry. It is a derivative of the amino acid histidine, with two di-tert-butyl-dicarbonate (Boc) protecting groups attached to the N-terminal amine and the imidazole nitrogen. Boc protecting groups are commonly used in peptide synthesis to prevent unwanted reactions at specific functional groups within the peptide chain. N(ALPHA) N-(IM)-DI-BOC-L-HISTIDINE is often used as a building block for the synthesis of histidine-containing peptides and proteins. It is also used in the development of pharmaceuticals and other bioactive compounds due to its ability to modulate biological processes and protein interactions. Overall, N(ALPHA) N-(IM)-DI-BOC-L-HISTIDINE is an important chemical in the field of organic and biochemistry with various potential applications.

InChI:InChI=1/C17H27N3O6/c1-16(2,3)25-14(22)19-12(13(21)24-7)8-11-9-20(10-18-11)15(23)26-17(4,5)6/h9-10,12H,8H2,1-7H3,(H,19,22)/t12-/m0/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 1499-46-3 L-Histidine methyl ester 
• 71-00-1 L-histidine 
• 4467-54-3 l-histidine methyl ester dihydrochloride 
• 1499-46-3 L-histidine methyl ester 

Downstream Products

• 2002-22-4 2-mercapto-L-histidine 
• 2488-14-4 (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(1H-imidazol-4-yl)propanoate 

Relevant articles and documents

Synthesis of Imidazole and Histidine-Derived Cross-Linkers as Analogues of GOLD and Desmosine

Amino acid derivatives with a central cationic heterocyclic core (e.g., imidazolium) are biologically relevant cross-linkers of proteins and advanced glycation end (AGE) products. Here, imidazolium-containing cross-linkers were synthesized from imidazole or histidine by N-alkylation employing aspartate- and glutamate-derived mesylates as key step. Biological investigations were carried out to probe the biocompatibility of these compounds.

Benzoazepine-Fused Isoindolines via Intramolecular (3 + 2)-Cycloadditions of Azomethine Ylides with Dinitroarenes

Aminobenzaldehydes bearing a pendant 3,5-dinitrophenyl group react thermally with N-substituted α-amino acids to form unprecedented benzoazepine-fused isoindolines. The reaction proceeds via a dearomatization/rearomatization sequence involving an intramolecular (3 + 2)-cycloaddition between the in situ formed azomethine ylide and the dinitroarene. Various glycine derivatives are tolerated as well as branched substrates based on cyclic, α-mono-, and α,α-disubstituted amino acids, giving single diastereomers in many cases. The method is scalable and gives products with a nitro group ready for further manipulation.

Allylpalladium(II) histidylidene complexes and their application in Z-selective transfer semihydrogenation of alkynes

We have studied the use of amino acid histidine as a precursor for N-heterocyclic carbene (NHC) ligands. This natural amino acid possesses an imidazole substituent, which makes it an interesting NHC precursor that contains both an acid and an amino functi