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CAS 13058-16-7

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N-CBZ-DL-Tryptophan

Description:
N-CBZ-DL-Tryptophan, also known as N-carbobenzyloxy-DL-tryptophan, is an amino acid derivative characterized by the presence of a carbobenzyloxy (CBZ) protecting group on the amino group of tryptophan. This compound is a white to off-white crystalline powder, soluble in organic solvents such as dimethyl sulfoxide (DMSO) and methanol, but generally insoluble in water. The CBZ group serves to protect the amino functionality during peptide synthesis, making it a valuable intermediate in the production of peptides and proteins. N-CBZ-DL-Tryptophan retains the essential properties of tryptophan, including its role as a precursor for serotonin and melatonin, and its involvement in protein synthesis. The DL designation indicates that the substance is a racemic mixture of both D- and L-tryptophan enantiomers. This compound is utilized in various biochemical applications, including research in neurochemistry and the synthesis of pharmaceuticals. Proper handling and storage are essential due to its potential reactivity and the need for protection from moisture and light.
Formula:C19H18N2O4
InChI:InChI=1/C19H18N2O4/c22-18(23)17(10-14-11-20-16-9-5-4-8-15(14)16)21-19(24)25-12-13-6-2-1-3-7-13/h1-9,11,17,20H,10,12H2,(H,21,24)(H,22,23)
InChI key:InChIKey=AHYFYYVVAXRMKB-UHFFFAOYSA-N
SMILES:C(C(NC(OCC1=CC=CC=C1)=O)C(O)=O)C=2C=3C(NC2)=CC=CC3
Synonyms:
  • 2-[[(Benzyloxy)carbonyl]amino]-3-(1H-indol-3-yl)propanoic acid
  • <span class="text-smallcaps">DL</span>-(Carbobenzyloxy)tryptophan
  • <span class="text-smallcaps">DL</span>-Tryptophan, N-[(phenylmethoxy)carbonyl]-
  • Carbobenzoxytryptophan
  • Cbz-<span class="text-smallcaps">D</smallcap><smallcap>L</span>-tryptophan
  • Cbz-DL-tryptophan
  • N-(Benzyloxycarbonyl)-<span class="text-smallcaps">DL</span>-tryptophan
  • N-Carbobenzoxy-DL-tryptophan
  • N-Carbobenzyloxy-<span class="text-smallcaps">DL</span>-tryptophan
  • N-Carbobenzyloxy-DL-tryptophan
  • See more synonyms
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