Z-L-Phenylalanine N-carboxyanhydride

Z-L-Phenylalanine N-carboxyanhydride is a phenylalanine-derived N-carboxyanhydride (NCA) in which the amino acid nitrogen is incorporated into a cyclic anhydride, bearing a Z (benzyloxycarbonyl) protecting group on the nitrogen and a phenyl side chain characteristic of L-phenylalanine. The molecule contains the reactive NCA carbonyl functionality within the anhydride ring alongside the benzyloxycarbonyl (Z) carbamate and the pendant benzyl-substituted phenyl group, with stereochemistry corresponding to the L-phenylalanine precursor as indicated by the product name. It is employed as a peptide-building intermediate in controlled polymerization and solid-phase or solution-phase peptide synthesis workflows, where the NCA ring can undergo ring-opening to generate growing peptide chains with phenylalanine residues under conditions compatible with carbamate-protected termini.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.

CAT No: CP01626

CAS No:25613-60-9

Synonyms/Alias:25613-60-9;Z-PHE-NCA;Z-L-PhenylalanineN-carboxyanhydride;ZINC100118931;HE024503;3-(Benzyloxycarbonyl)-4beta-benzyloxazolidine-2,5-dione;3-Oxazolidinecarboxylicacid,2,5-dioxo-4-(phenylmethyl)-,phenylmethylester,(4S)-

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M.F/Formula
C18H15NO5
M.W/Mr.
325.3
Abbr
Z-Phe-NCA
InChI
1S/C18H15NO5/c20-16-15(11-13-7-3-1-4-8-13)19(18(22)24-16)17(21)23-12-14-9-5-2-6-10-14/h1-10,15H,11-12H2/t15-/m0/s1
InChI Key
XGEVCUXPCGZQLQ-HNNXBMFYSA-N
Canonical SMILES
C1=CC=C(C=C1)CC2C(=O)OC(=O)N2C(=O)OCC3=CC=CC=C3

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