393568-74-6

Basic information

• Product Name: (R)-2-((tert-Butoxycarbonyl)amino)-3-(1-trityl-1H-imidazol-4-yl)propionic acid
• Synonyms: (R)-2-((tert-Butoxycarbonyl)amino)-3-(1-trityl-1H-imidazol-4-yl)propionic acid;N-[(1,1-Dimethylethoxy)carbonyl]-1-(triphenylmethyl)-D-histidine;(Tert-Butoxy)Carbonyl D-His(Trt)-OH
• CAS NO: 393568-74-6
• Molecular Formula: C30H31N3O4
• Molecular Weight: 497.58484
• Mol File: 393568-74-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-2-((tert-Butoxycarbonyl)amino)-3-(1-trityl-1H-imidazol-4-yl)propionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-((tert-Butoxycarbonyl)amino)-3-(1-trityl-1H-imidazol-4-yl)propionic acid(393568-74-6)
• EPA Substance Registry System: (R)-2-((tert-Butoxycarbonyl)amino)-3-(1-trityl-1H-imidazol-4-yl)propionic acid(393568-74-6)

Safety Data

• Hazardous Substances Data: 393568-74-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry:
(R)-2-((tert-Butoxycarbonyl)amino)-3-(1-trityl-1H-imidazol-4-yl)propionic acid is used as a building block for the synthesis of complex organic molecules, taking advantage of its Boc protecting group to facilitate the formation of peptide bonds and other organic reactions.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (R)-2-((tert-Butoxycarbonyl)amino)-3-(1-trityl-1H-imidazol-4-yl)propionic acid is used as a key intermediate in the development of new drugs, particularly in the synthesis of peptide-based pharmaceuticals. Its unique structure and functional groups make it a promising candidate for the design of novel therapeutic agents.
Used in Bioconjugation:
(R)-2-((tert-Butoxycarbonyl)amino)-3-(1-trityl-1H-imidazol-4-yl)propionic acid is employed as a bioconjugation agent, allowing for the attachment of various biomolecules, such as proteins, nucleic acids, or other small molecules, to create conjugates with enhanced properties or functionalities.
Used in Chemical Biology Research:
(R)-2-((tert-Butoxycarbonyl)amino)-3-(1-trityl-1H-imidazol-4-yl)propionic acid is utilized in chemical biology research as a tool to study the interactions between biomolecules and to develop new methods for the manipulation of biological systems. Its unique structure and functional groups enable the exploration of novel chemical reactions and the discovery of new biological activities.

Upstream product

• 71-00-1 L-histidine 
• 20866-46-0 N,1'-bis[(1,1-dimethylethoxy)carbonyl]-L-histidine 
• 17791-52-5 N-(tert-butoxycarbonyl)-L-histidine 
• 74853-62-6 N^α,N^im-ditritylhistidine 
• 32946-53-5 N^im-trityl-L-histidine hydrochloride 
• 24424-99-5 di-tert-butyl dicarbonate 
• 68262-63-5 N^α-benzyloxycarbonyl-N^im-triphenylmethyl-L-histidine methyl ester 
• 15545-10-5 Z-His-OMe 
• 14997-58-1 N-[(benzyloxy)carbonyl]-L-histidine 
• 1499-46-3 L-Histidine methyl ester 
• 62715-28-0 N^im-triphenylmethyl-L-histidine methyl ester 
• 40917-50-8 1,N^α-bis-benzyloxycarbonyl-histidine methyl ester 
• 76-83-5 trityl chloride 
• 62697-87-4 N^α-(tert-butyloxy)carbonyl-N^im-triphenylmethyl-L-histidine methyl ester 

Downstream Products

• 1615698-00-4 H-His-D-Trp-Ala-aza(N^δ,N^δ-diallyl)Orn-D-Phe-Lys-NH₂ 
• 1615698-01-5 H-His-D-Trp-Ala-aza-3-(piperidin-1-yl)propylglycinyl-D-Phe-Lys-NH₂ 
• 1615698-02-6 H-His-D-Trp-Ala-aza-(3-morpholin-1-ylpropyl)glycinyl-D-Phe-Lys-NH₂ 
• 1615698-03-7 H-His-D-Trp-Ala-aza(N^δ-allyl)Orn-D-Phe-Lys-NH₂ 
• 1615698-04-8 H-His-D-Trp-Ala-aza(N^ε,N^ε-diallyl)Lys-D-Phe-Lys-NH₂ 
• 1615698-05-9 H-His-D-Trp-Ala-aza-(N^ε-methyl-N^ε-benzyl)Lys-D-Phe-Lys-NH₂ 
• 1615698-06-0 H-His-D-Trp-Ala-aza-(N^ε-methoxyethyl)Lys-D-Phe-Lys-NH₂ 
• 1615698-10-6 His-D-Trp-Ala-Trp-D-Phe-azaGly(4-(N,N-dimethyl)aminobutyl)-NH₂ 
• 1615698-09-3 His-D-Trp-Ala-Trp-D-Phe-aza-(N^ε-methyl)Lys-NH₂ 
• 1615698-08-2 H-His-D-Trp-aza-N^ε-(4-piperidin-1-yl)butylglycine-Trp-D-Phe-Lys-NH₂ 

Relevant articles and documents

Compounds and inhibitors of phospholipases

The present invention relates generally to amino acid derivatives and to methods of making the same. In particular, the invention relates to compounds bearing a stereochemical identity, that is, the same stereochemistry, with the chiral α-carbon of D-α-amino acids and their use in methods of therapy, including the treatment of inflammatory diseases, and to compositions and enantiomeric mixtures containing them.

Synthesis and evaluation of deglycobleomycin A2 analogues containing a tertiary N-methyl amide and simple ester replacement for the L-histidine secondary amide: Direct functional characterization of the requirement for secondary amide metal complexation

The synthesis and comparative examination of 3-5, analogues of deglycobleomycin A2 (2) which address the inferred importance of the L-histidine secondary amide directly, are detailed. The agent 3 lacks only the L-histidine β-hydroxy group of deglycobleomycin A2 and the corresponding agents 4 and 5 incorporate a tertiary N-methyl amide and simple ester in place of the L-histidine secondary amide. The DNA cleavage properties of 3 proved essentially indistinguishable from those of deglycobleomycin A2 (2) confirming that the distinctions between bleomycin A2 (1) and deglycobleomycin (2) are due to the removal of the disaccharide and not the introduction of the L-histidine free β-hydroxy group. The agents 4 and 5 containing a tertiary N-methyl amide and ester in place of the L-histidine secondary amide were found to cleave duplex DNA but to do so in a nonsequence selective fashion with a substantially reduced efficiency and a diminished double to single strand cleavage ratio that are only slightly greater than that of free iron itself. These latter observations establish the functional requirement for the L-histidine secondary amide and are consistent with the proposals that the L-histidine deprotonated secondary amide is required for functional metal chelation and activity.

IMPROVED METHODS OF OBTAINING Nim-TRITYL-SUBSTITUTED HISTIDINE DERIVATIVES

Two variants are proposed for the synthesis of Nα-Boc-Nim-tritylhistidiine.The first variant starts from Nα,Nim-di-Boc-histidine, from which the Nim-Boc group is removed with hydrazine hydrate.The Nα-Boc-histidine formed is esterified with chlorotrimethylsilane, tritylated in the imidazole group, and, after the elimination of the trimethylsilyl protection from the carboxyl group, Nα-Boc-Nim-tritylglycine is obtained with a yield of 80percent.The second variant starts from Nα,Nim-ditritylhistidine, which, by treatment with hydrochloric acid in acetone and then with dilute ammonia, is converted into Nim- tritylhistidine.From this, by acylation with di-tert-butyl pyrocarbonate, Nα-Boc-Nim-tritylhistidine is obtained with a yield of 91percent.The acylation of Nim-tritylhistidine with other alkoxycarbonylating reagents leads to Nα-tert-amyl-, Nα-benzyl-, and Nα-4-methoxybenzyloxycarbonyl derivatives of Nim-tritylhistidine.