1515861-58-1

Basic information

• Product Name: (2-methylcycloprop-2-en-1-yl)methyl (4-nitrophenyl) carbonate
• Synonyms: (2-methylcycloprop-2-en-1-yl)methyl (4-nitrophenyl) carbonate
• CAS NO: 1515861-58-1
• Molecular Weight: 249.223
• Mol File: 1515861-58-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (2-methylcycloprop-2-en-1-yl)methyl (4-nitrophenyl) carbonate(CAS DataBase Reference)
• NIST Chemistry Reference: (2-methylcycloprop-2-en-1-yl)methyl (4-nitrophenyl) carbonate(1515861-58-1)
• EPA Substance Registry System: (2-methylcycloprop-2-en-1-yl)methyl (4-nitrophenyl) carbonate(1515861-58-1)

Safety Data

• Hazardous Substances Data: 1515861-58-1(Hazardous Substances Data)

Upstream product

• 33002-26-5 2-methyl-3-(trimethylsilyl)cycloprop-3-ene-1-carboxylic acid ethyl ester 
• 5809-04-1 ethyl ester of 1-methylcyclopropene-3-carboxylic acid 
• 79671-36-6 (2-methyl-3-(trimethylsilyl)-cycloprop-2-en-1-yl)methanol 
• 7693-46-1 4-Nitrophenyl chloroformate 
• 1407593-23-0 C₅H₈O 

Relevant articles and documents

Improved cyclopropene reporters for probing protein glycosylation

Cyclopropenes have emerged as a new class of bioorthogonal chemical reporters. These strained rings can be metabolically introduced into target biomolecules and covalently modified via mild cycloaddition chemistries. While versatile, existing cyclopropene scaffolds are inefficient reporters of protein glycosylation, owing to their branched structures and sluggish rates of reactivity. Here we describe a set of cyclopropenes for the robust detection of glycans on cell surfaces and isolated proteins. These scaffolds comprise carbamate linkages that are compatible with cellular biosynthetic pathways and exhibit rapid cycloaddition rates. Furthermore, these probes can be used in tandem with other classic bioorthogonal motifs - including azides and alkynes - to examine multiple biomolecules in tandem. This journal is the Partner Organisations 2014.

Live-cell imaging and profiling of c-Jun N-terminal kinases using covalent inhibitor-derived probes

c-Jun N-terminal kinases (JNKs) are involved in critical cellular functions. Herein, small-molecule JNK-targeting probes are reported based on a covalent inhibitor. Together with newly developed two-photon fluorescence Turn-ON reporters and chemoproteomic studies, we showed that some probes may be suitable for live-cell imaging and profiling of JNKs.

Rapid labeling of metabolically engineered cell-surface glycoconjugates with a carbamate-linked cyclopropene reporter

Metabolic oligosaccharide engineering is a valuable tool to monitor cellular carbohydrates. Here, we report the synthesis of a novel N-acyl-mannosamine derivative bearing a methylcyclopropene tag that is attached to the sugar via a carbamate moiety. This derivative undergoes rapid Diels-Alder reaction with inverse electron demand. We demonstrate that the cell's biosynthetic machinery incorporates this non-natural mannosamine derivative into glycoconjugates that can, subsequently, be labeled within less than 10 min with a new sulfo-Cy3-tetrazine conjugate. Using this tetrazine-dye conjugate for the detection of the methylcyclopropene-tagged mannosamine derivative, we could achieve dual labeling of two different metabolically incorporated sugars combining a Diels-Alder reaction with inverse electron demand and a strain-promoted azide-alkyne cycloaddition which are carried out simultaneously in a single step.