101399-00-2

Basic information

• Product Name: (S)-tert-butyl 2-(2-(((benzyloxy)carbonyl)amino)acetamido)-3-phenylpropanoate
• CAS NO: 101399-00-2
• Molecular Weight: 412.486
• Mol File: 101399-00-2.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (S)-tert-butyl 2-(2-(((benzyloxy)carbonyl)amino)acetamido)-3-phenylpropanoate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-tert-butyl 2-(2-(((benzyloxy)carbonyl)amino)acetamido)-3-phenylpropanoate(101399-00-2)
• EPA Substance Registry System: (S)-tert-butyl 2-(2-(((benzyloxy)carbonyl)amino)acetamido)-3-phenylpropanoate(101399-00-2)

Safety Data

• Hazardous Substances Data: 101399-00-2(Hazardous Substances Data)

Upstream product

• 1212-53-9 methyl N-benzyloxycarbonylglycinate 
• 16874-17-2 L-phenylalanine tert-butyl ester 
• 203640-50-0 Z-Gly 2,2,2-trifluoroethyl ester 
• 16881-34-8 N-benzyloxycarbonyl-L-phenylalanine t-butyl ester 
• 1161-13-3 N-Cbz-L-Phe 
• 15100-75-1 L-phenylalanine tert-butyl ester hydrochloride 
• 159396-61-9 benzyl 2,5-dioxo-oxazolidine-3-carboxylate 
• 1138-80-3 N-(Benzyloxycarbonyl)glycine 

Downstream Products

• 1170-76-9 Z-Gly-(L)-Phe 
• 6206-42-4 N-benzyloxycarbonylglycyl-L-phenylalanine methyl ester 
• 16874-18-3 Glycyl-(S)-phenylalanine tert-butyl ester 
• 501928-24-1 (S)-tert-butyl 2-(2-((diphenylmethylene)amino)acetamido)-3-phenylpropanoate 

Relevant articles and documents

Stereocontrolled [11C]Alkylation of N-Terminal Glycine Schiff Bases To Obtain Dipeptides

The use of various quaternary ammonium salts as chiral phase-transfer catalysts allowed effective and stereoselective radiochemical [11C]alkylation to obtain functionalized dipeptides. We herein report a broadly applicable procedure for the asymmetric [11C]alkylation of dipeptides to give labeled N-terminal peptides by using different [11C]alkyl halides. Contended stereoselectivities of the reactions were observed by using 11C-labeled alkyl halides, [11C]methyl iodide and [11C]benzyl iodide, and diastereomeric ratios with different specialized catalysts of 95:5 and 90:10 were achieved, respectively. Accordingly, the straightforward synthesis of enantioenriched compounds should play a vital role in peptide-based radiopharmaceutical development and positron emission tomography imaging.

Enzymatic synthesis of activated esters and their subsequent use in enzyme-based peptide synthesis

Chemoenzymatic peptide synthesis is potentially the most cost-efficient technology for the synthesis of short and medium-sized peptides. However, there are still some limitations when challenging peptides, e.g. containing sterically demanding acyl donors, non-proteinogenic amino acids or proline residues, are to be synthesized. To remedy these limitations, special ester moieties have been used that are specifically recognized by the enzyme, e.g. guanidinophenyl, carboxamidomethyl (Cam) or trifluoroethyl (Tfe) esters, which, unfortunately, are notoriously difficult to synthesize chemically. Herein, we demonstrate that Cam and Tfe esters are very useful for Alcalase-CLEA mediated peptide synthesis using sterically demanding and non-proteinogenic acyl donors as well as poor nucleophiles, and combinations thereof. Furthermore, these esters can be efficiently synthesized by using the lipase Cal-B or Alcalase-CLEA. Finally, it is shown that the ester synthesis by Cal-B and subsequent peptide synthesis by Alcalase-CLEA can be performed simultaneously using a two-enzyme-one-pot approach with glycolamide or 2,2,2-trifluoroethanol as additive.

Rapid, one-pot synthesis of urethane-protected tripeptides

Urethane-protected tripeptides are synthesized in solution, without isolation of purification of intermediates, using urethane-protected N-carboxyanhydrides as coupling reagents and hydrogenation for removal of N-protection.