CAS 74244-17-0
:N~2~-(tert-butoxycarbonyl)-L-alpha-asparagine
Description:
N~2~-(tert-butoxycarbonyl)-L-alpha-asparagine, commonly referred to as Boc-Asn, is a derivative of the amino acid asparagine, characterized by the presence of a tert-butoxycarbonyl (Boc) protecting group on the nitrogen atom of the side chain. This modification enhances the stability and solubility of the molecule, making it useful in peptide synthesis and other biochemical applications. The Boc group is a common protecting group in organic synthesis, allowing for selective reactions without interfering with the amino acid's functional groups. Boc-Asn is typically a white to off-white crystalline solid, soluble in polar solvents like water and methanol, and exhibits a neutral pH in solution. Its structure includes both an amine and a carboxylic acid functional group, contributing to its properties as a zwitterion at physiological pH. The compound is utilized in the synthesis of peptides and proteins, particularly in the context of solid-phase peptide synthesis, where protecting groups are essential for controlling reactivity during the assembly of complex molecules.
Formula:C9H16N2O5
InChI:InChI=1/C9H16N2O5/c1-9(2,3)16-8(15)11-5(7(10)14)4-6(12)13/h5H,4H2,1-3H3,(H2,10,14)(H,11,15)(H,12,13)/t5-/m0/s1
SMILES:CC(C)(C)OC(=N[C@@H](CC(=O)O)C(=N)O)O
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