"Protection of the amino group in amino acids plays a crucial role in peptide synthesis. N-Benzyl groups (N-Bn) are especially useful for replacing the N-H protons in primary and secondary amines when exposed to organometallic reagents or metal hydrides. … Acylation of primary and secondary amines with acetic anhydride or acid chlorides furnishes the corresponding amides in which the basicity of the nitrogen is reduced, making them less susceptible to attack by electrophilic reagents. … Treatment of primary and secondary amines with methyl or ethyl chloroformate in the presence of a tertiary-amine furnishes the corresponding methyl and ethyl carbamates, respectively. The protected amines behave like amides; hence, they no longer act as nucleophiles. … The benzyloxycarbonyl group (abbreviated as Cbz or Z) is one of the most important nitrogen-protecting groups in organic synthesis, especially in peptide synthesis. … The t-butoxycarbonyl group (Boc) is another widely used protecting group for primary and secondary amine."
Quote Details
Added by wikiquote-import-bot
Unverified quote
0 likes
Original Language: English
Available Languages (1)
Sources
George S. Zweifel and Michael H. Nantz, Modern Organic Synthesis (2006), Ch. 3 : The Concept of Protecting Functional Groups
https://en.wikiquote.org/wiki/Protecting_group
Revision History
No revisions have been submitted for this quote.
Categories
Protecting group
3 quotes on TrueQuotesView all quotes by Protecting group →
Related Quotes
"The protecting group reagent must react selectively (kinetic chemoselectivity) in good yield to give a protected subs…"
"The most important protecting groups for alcohols are ethers and mixed acetals. … Methyl ethers are readily accessibl…"
"[M]ost TiO2 has been synthesized from the mineral , FeTiO3 , using the "sulphate" or "chloride" process for nearly 10…"
"There is inadequate evidence in humans for the carcinogenicity of titanium dioxide. ...There is sufficient evidence i…"
"The Working Group considered the body of evidence regarding the pathways and mechanisms by which titanium dioxide and…"
"TiO2 has been classified in humans and animals as biologically inert... and is widely considered to be a "natural" ma…"
"Most titanium dioxide pigment is produced from mineral concentrates by the chloride or sulfate process, either as the…"
"Exposure levels [to titanium dioxide]... are assumed to be low... with the possible exception of workers who handle l…"
"In two studies of rats that inhaled titanium dioxide, one observed an excess incidence of lung tumours... No increase…"
"Titanium dioxide is obtained from a variety of ores that contain [FeTiO3], [TiO2, but may contain up to 10% iron and …"