154187-40-3

Basic information

• Product Name: 2-(2-nitrophenyl)propyl carbonochloridate
• Synonyms: 2-(2-nitrophenyl)propyl carbonochloridate
• CAS NO: 154187-40-3
• Molecular Weight: 229.62
• Mol File: 154187-40-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-(2-nitrophenyl)propyl carbonochloridate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-nitrophenyl)propyl carbonochloridate(154187-40-3)
• EPA Substance Registry System: 2-(2-nitrophenyl)propyl carbonochloridate(154187-40-3)

Safety Data

• Hazardous Substances Data: 154187-40-3(Hazardous Substances Data)

Upstream product

• 577-59-3 2-acetylnitrobenzene 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 80379-10-8 1-(2-nitrophenyl)ethan-1-ol 
• 503-38-8 trichloromethyl chloroformate 

Downstream Products

• 219646-74-9 ((E)-(1S,2R)-2-Hydroxy-1-hydroxymethyl-heptadec-3-enyl)-carbamic acid 1-(2-nitro-phenyl)-ethyl ester 
• 219646-77-2 [(4R,5S)-2-(2-Cyano-ethoxy)-2-oxo-4-((E)-pentadec-1-enyl)-2λ⁵-[1,3,2]dioxaphosphinan-5-yl]-carbamic acid 1-(2-nitro-phenyl)-ethyl ester 
• 219646-80-7 [(4R,5S)-2-Hydroxy-2-oxo-4-((E)-pentadec-1-enyl)-2λ⁵-[1,3,2]dioxaphosphinan-5-yl]-carbamic acid 1-(2-nitro-phenyl)-ethyl ester 
• 298699-74-8 N²-{[4-(tert-butyl)phenoxy]acetyl}-2'-deoxy-3'-O-{[2-(2-nitrophenyl)propoxy]carbonyl}guanosine 
• 298699-73-7 N⁶-{[4-(tert-butyl)phenoxy]acetyl}-2'-deoxy-3'-O-{[2-(2-nitrophenyl)propoxy]carbonyl}adenosine 
• 298699-72-6 N⁴-{[4-(tert-butyl)phenoxy]acetyl}-2'-deoxy-3'-O-{[2-(2-nitrophenyl)propoxy]carbonyl}cytidine 
• 298699-71-5 3'-O-{[2-(2-nitrophenyl)propoxy]carbonyl}thymidine 

Relevant articles and documents

Studies on Aculeines: Synthetic Strategy to the Fully Protected Protoaculeine B, the N-Terminal Amino Acid of Aculeine B

A synthetic strategy for accessing protoaculeine B (1), the N-terminal amino acid of the highly modified peptide toxin aculeine, was developed via the synthesis of the fully protected natural homologue of 1 with a 12-mer poly(propanediamine). The synthesis of mono(propanediamine) analog 2, as well as core amino acid 3, was demonstrated by this strategy. New amino acid 3 induced convulsions in mice; however, compound 2 showed no such activity.

Photosensitive caged macromolecules

Disclosed is a method for preparing a photosensitive peptide which is capable of being activated or deactivated in a biological system, including the steps of: (a) providing an amino acid including a photolabile molecule; and (b) incorporating the amino acid into a peptide during synthesis, wherein incorporation of the amino acid into the peptide produces a photosensitive peptide. Also disclosed is a method of introducing a photosensitive cleavage site into a synthetic peptide, including synthesizing a synthetic peptide having at least one photolabile amino acid, wherein the photolabile amino acid is positioned within the synthetic peptide so that upon irradiation the synthetic peptide is cleaved.

Synthesis, photoreactivity and cytotoxic activity of caged compounds of L-leucyl-L-leucine methyl ester, an apoptosis inducer

L-Leucyl-L-leucine methyl ester (Leu-Leu-OMe), an apoptosis inducer in natural killer cells and macrophages, was caged with trans-o-hydroxycinnamoyl (3a-d), trans-o-mercaptocinnamoyl (4) and o-nitrobenzyl derivatives (5a, b), and the photochemical reactivity of these derivatives in phosphate-buffered saline containing 1% dimethyl sulfoxide and their immunological properties were studied. All of the derivatives exhibited absorption at wavelengths longer than the UVB region. Although 3a-d and 4 were expected to isomerize to a cis isomer, which then cyclizes intramolecularly to give LeuLeu-OMe and a coumarin derivative, cyclization efficiency was not satisfactory except for 3a. However, 3a itself caused necrosis (cell swelling) of U937 cells (a myeloid cell line). In contrast, 5a and b released Leu-Leu-OMe quickly and efficiently and did not affect U937 cells. Although irradiated 5b induced necrosis, irradiated 3a and 5a induced apoptosis in these cells, as evidenced by a decrease in cell size.