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The tert-butyloxycarbonyl protecting group or tert-butoxycarbonyl protecting group [1] (BOC group) is an acid-labile protecting group used in organic synthesis. The BOC group can be added to amines under aqueous conditions using di- tert -butyl dicarbonate in the presence of a base such as sodium hydroxide :
The Boc group can later be removed from the amine using moderately strong acids (e.g., trifluoroacetic acid). Thus, Boc serves as a protective group, for instance in solid phase peptide synthesis. Boc-protected amines are unreactive to most bases and nucleophiles, allowing for the use of the fluorenylmethyloxycarbonyl group (Fmoc) as an ...
In this example, the second reactive group (amine/acid) in each of the starting materials bears a protecting group. In organic chemistry , peptide synthesis is the production of peptides , compounds where multiple amino acids are linked via amide bonds, also known as peptide bonds .
Orthogonal protection is a strategy allowing the specific deprotection of one protective group in a multiply-protected structure. For example, the amino acid tyrosine could be protected as a benzyl ester on the carboxyl group, a fluorenylmethylenoxy carbamate on the amine group, and a tert-butyl ether on the phenol
Amino acids with the structure NH + 3 −CXY−CXY−CO − 2, such as β-alanine, a component of carnosine and a few other peptides, are β-amino acids. Ones with the structure NH + 3 −CXY−CXY−CXY−CO − 2 are γ-amino acids, and so on, where X and Y are two substituents (one of which is normally H). [7]
Di-tert-butyl-iminodicarboxylate is an organic compound that can be described with the formula [(CH 3) 3 COC(O)] 2 NH.It is a white solid that is soluble in organic solvents. The compound is used as a reagent for the preparation of primary amines from alkyl halides
The fluorenylmethoxycarbonyl protecting group (Fmoc) is a base-labile amine protecting group used in organic synthesis, particularly in peptide synthesis. [1] It is popular for its stability toward acids and hydrolysis and its selective removal by weak bases, such as piperidine , without affecting most other protecting groups or sensitive ...
Alanine (symbol Ala or A), [4] or α-alanine, is an α-amino acid that is used in the biosynthesis of proteins. It contains an amine group and a carboxylic acid group, both attached to the central carbon atom which also carries a methyl group side chain. Consequently it is classified as a nonpolar, aliphatic α-amino acid.