N-Benzyloxycarbonyl-D-phenylalanine TCI C0662

Chemical Identity

Other names: Z-D-Phe-OH · N-Cbz-D-phenylalanine · Z-D-Phe-OH · N-Carbobenzoxy-D-phenylalanine
CAS No.: 2448-45-5
PubChem: CID 675678·SID 87565752
Formula: C17H17NO4
Molecular weight: 299.33 g/mol
Purity: >98.0%(T)

Full identifiers (IUPAC, SMILES, InChIKey)

IUPAC: (2R)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoic acid
SMILES: C1=CC=C(C=C1)CC(C(=O)O)NC(=O)OCC2=CC=CC=C2
InChIKey: RRONHWAVOYADJL-OAHLLOKOSA-N
MDL: MDL00063151

Rp 530.250,00

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TCI C0662 N-Benzyloxycarbonyl-D-phenylalanine (CAS 2448-45-5), or Z-D-Phe-OH, is the D-enantiomer of Cbz-protected phenylalanine. Incorporating D-residues into peptides typically improves resistance to proteolytic degradation, which makes this reagent valuable in peptidomimetic and bioactive peptide design. The benzyloxycarbonyl group protects the amino function during coupling and is removed by catalytic hydrogenolysis, allowing orthogonal use alongside acid-labile protecting groups. AMI Scientific provides this TCI product in 1 g and 5 g packs for research use; keep it tightly closed in a cool, dry, light-protected place and refer to the manufacturer's Safety Data Sheet before handling.

TCI brochures (PDF)

Amino Acids and Peptide Synthesis Reagents 2025-08-14 · p. 17

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Ambroso et al. (1994). In vitro embryotoxicity of the cysteine proteinase inhibitors benzyloxycarbonyl‐phenylalanine‐alanine‐diazomethane (Z‐Phe‐Ala‐CHN2) and benzyloxycarbony1‐phenylalanine‐phenylalanine‐diazomethane (Z‐Phe‐Phe‐CHN2). Teratology doi:10.1002/tera.1420500307

References were compiled automatically from Crossref and every DOI was verified to exist. AMI Scientific is not affiliated with the authors or the publishers.