128228-48-8

Basic information

• Product Name: {(S)-1-[4-(1H-Indol-3-ylmethyl)-5-oxo-4,5-dihydro-oxazol-2-yl]-ethyl}-carbamic acid benzyl ester
• CAS NO: 128228-48-8
• Molecular Weight: 391.426
• Mol File: 128228-48-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: {(S)-1-[4-(1H-Indol-3-ylmethyl)-5-oxo-4,5-dihydro-oxazol-2-yl]-ethyl}-carbamic acid benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: {(S)-1-[4-(1H-Indol-3-ylmethyl)-5-oxo-4,5-dihydro-oxazol-2-yl]-ethyl}-carbamic acid benzyl ester(128228-48-8)
• EPA Substance Registry System: {(S)-1-[4-(1H-Indol-3-ylmethyl)-5-oxo-4,5-dihydro-oxazol-2-yl]-ethyl}-carbamic acid benzyl ester(128228-48-8)

Safety Data

• Hazardous Substances Data: 128228-48-8(Hazardous Substances Data)

Upstream product

• 119645-65-7 (2S)-2-[((2S)-2-{[(benzyloxy)carbonyl]amino}propanoyl)amino]-3-(1H-indol-3-yl)propanoic acid 

Downstream Products

• 119645-71-5 1-((S)-1-Benzyloxycarbonylamino-ethyl)-4,9-dihydro-3H-β-carboline-3-carboxylic acid 

Relevant articles and documents

Quantitative description of epimerization pathways using the carbodiimide method in the synthesis of peptides

The mechanism of epimerization in carbodiimide synthesis has been investigated by varying the side chain of the activated acids. A series of peptides N-benzyloxycarbonyl-Ala-Xaa-OH with 20 different residues Xaa were coupled with valine methyl ester in dichloromethane and dimethylformamide. The kinetic data and the extent of epimerization were determined for the peptide synthesis and the aminolysis of isolated oxazol-5(4H)-ones by means of IR spectroscopy, polarimetry and reversed-phase HPLC. Combining the results we succeeded for the first time in a quantitative description of the overlapping pathways of epimerization and their dependence on amino acid sequence during carbodiimide synthesis.

Derivatives of 3,4-dihydro-β-carboline-3-carboxylic acid from C-terminal tryptophan-containing peptides. Synthesis and properties

C-terminal tryptophan containing peptides have been converted into 1-peptidyl-3,4-dihydro-β-carboline-3-carboxylic acids by acid catalyzed isomerization of their azlactone derivatives. The main properties of these abnormal peptides are a strong absorption around 360 nm an intense fluoroscence and ability to generate reactive carbanions when dissolved in basic media. This tryptophan conversion takes place with high yield and is of general applicability.