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CAS 144701-21-3

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N-(9-Fluorenylmethoxycarbonyl)-<span class="text-smallcaps">DL</span>-norvaline

Description:
N-(9-Fluorenylmethoxycarbonyl)-DL-norvaline, commonly referred to as Fmoc-DL-norvaline, is a derivative of the amino acid norvaline, modified with a 9-fluorenylmethoxycarbonyl (Fmoc) protecting group. This compound is primarily utilized in peptide synthesis, particularly in solid-phase peptide synthesis (SPPS), where the Fmoc group serves as a protective moiety for the amino group, allowing for selective deprotection and coupling reactions. The presence of the Fmoc group enhances the solubility of the amino acid in organic solvents, facilitating its incorporation into growing peptide chains. Fmoc-DL-norvaline is characterized by its stability under basic conditions and its ability to undergo deprotection under mild acidic conditions, typically using piperidine. The compound is also notable for its role in studies related to protein structure and function, as norvaline is a non-polar, branched-chain amino acid that can influence the hydrophobic interactions within peptides and proteins. Overall, Fmoc-DL-norvaline is an important building block in the field of synthetic organic chemistry and biochemistry.
Formula:C20H21NO4
InChI:InChI=1S/C20H21NO4/c1-2-7-18(19(22)23)21-20(24)25-12-17-15-10-5-3-8-13(15)14-9-4-6-11-16(14)17/h3-6,8-11,17-18H,2,7,12H2,1H3,(H,21,24)(H,22,23)
InChI key:InChIKey=JBIJSEUVWWLFGV-UHFFFAOYSA-N
SMILES:C(OC(NC(CCC)C(O)=O)=O)C1C=2C(C=3C1=CC=CC3)=CC=CC2
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