177897-89-1

Basic information

• Product Name: Z-Glu(O-2-Ada)-OBzl
• CAS NO: 177897-89-1
• Molecular Weight: 505.611
• Mol File: 177897-89-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Z-Glu(O-2-Ada)-OBzl(CAS DataBase Reference)
• NIST Chemistry Reference: Z-Glu(O-2-Ada)-OBzl(177897-89-1)
• EPA Substance Registry System: Z-Glu(O-2-Ada)-OBzl(177897-89-1)

Safety Data

• Hazardous Substances Data: 177897-89-1(Hazardous Substances Data)

Upstream product

• 3705-42-8 Cbz-(L)-Glu-OBn 
• 538-75-0 dicyclohexyl-carbodiimide 
• 700-57-2 1-adamantanol 

Relevant articles and documents

Amino acids and peptides. XLIX. Synthesis of γ-2-adamantylglutamate and its evaluation for peptide synthesis

2-Adamantyl ester was examined for the selective protection of the γ- carboxyl function of the Glu residue, with the aim of preventing side reactions during peptide synthesis and increasing the solubility in organic solvents of peptide intermediates containing the Glu residue. Z-Glu(O-2- Ada)-OBzl was synthesized from Z-Glu-OBzl and adamantan-2-ol with the aid of dicyclohexylcarbodiimide (DCC) and 4-N,N-dimethylaminopyridine (DMAP) in AcOEt. The 2-adamantyl ester group was stable to TFA, 20% piperidine/DMF and 10% Et3N/DMF up to 24 h and was easily removed by MSA, 1 M TFMSA-thioanisole in TFA, and HF. Therefore, H-Glu-(O-2-Ada)-OH could be applied for peptide synthesis in both solution and solid phase methods in combination with a Boc or Fmoc group as the N2-protecting group. Boc-Glu(O-2-Ada)-OH was successfully employed for the synthesis of Bz-Ile-Glu-Gly-Arg-CH2Cl, an irreversible inhibitor of factor Xa.