895167-06-3

Basic information

• Product Name: 2-[2-tert-butoxycarbonylamino-3-(4-tert-butoxycarbonyloxy-phenyl)-propionylamino]-adamantane-2-carboxylic acid
• Synonyms: 2-[2-tert-butoxycarbonylamino-3-(4-tert-butoxycarbonyloxy-phenyl)-propionylamino]-adamantane-2-carboxylic acid
• CAS NO: 895167-06-3
• Molecular Weight: 558.672
• Mol File: 895167-06-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2-[2-tert-butoxycarbonylamino-3-(4-tert-butoxycarbonyloxy-phenyl)-propionylamino]-adamantane-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[2-tert-butoxycarbonylamino-3-(4-tert-butoxycarbonyloxy-phenyl)-propionylamino]-adamantane-2-carboxylic acid(895167-06-3)
• EPA Substance Registry System: 2-[2-tert-butoxycarbonylamino-3-(4-tert-butoxycarbonyloxy-phenyl)-propionylamino]-adamantane-2-carboxylic acid(895167-06-3)

Safety Data

• Hazardous Substances Data: 895167-06-3(Hazardous Substances Data)

Upstream product

• 42381-05-5 2-amino-2-adamantanecarboxylic acid 
• 20866-48-2 (S)-2-(tert-butoxycarbonylamino)-3-(4-(tert-butoxycarbonyloxy)phenyl)propanoic acid 

Downstream Products

• 910126-87-3 2-{2-[2-({2-[2-tert-butoxycarbonylamino-3-(4-tert-butoxycarbonyloxy-phenyl)-propionylamino]-adamantane-2-carbonyl}-amino)-acetylamino]-3-phenyl-propionylamino}-4-methylsulfanyl-butyric acid 
• 895167-16-5 ({2-[2-tert-butoxycarbonylamino-3-(4-tert-butoxycarbonyloxy-phenyl)-propionylamino]-adamantane-2-carbonyl}-amino)-acetic acid 
• 895167-15-4 ({2-[2-tert-butoxycarbonylamino-3-(4-tert-butoxycarbonyloxy-phenyl)-propionylamino]-adamantane-2-carbonyl}-amino)-acetic acid ethyl ester 

Relevant articles and documents

Tumor-cell-targeted methionine-enkephalin analogues containing unnatural amino acids: Design, synthesis, and in vitro antitumor activity

A series of new peptides (8-25) containing different unnatural amino acids of the adamantane type (1-6), was synthesized. Possible cytotoxic activity on human cervical adenocarcinoma (HeLa), larynx carcinoma (HEp-2), colon carcinomas (HT-29, Caco-2), poorly differentiated cells from lymph node metastasis of colon carcinoma (SW-620), mammary gland adenocarcinoma (MCF-7), and melanoma (HBL) cells were tested by the MTT assay. The results were compared with the effect of methionine-enkephalin (Tyr-Gly-Gly-Phe-Met, or opioid growth factor, OGF), and its shorter N-terminal fragments. Peptide analogues containing Cαα-dialkylated glycine (Aaa1, 1) or Cα-alkylated glycine (Aaa2, 2) amino acid residues showed antitumor activity against melanoma, larynx carcinoma, colon carcinomas, and colon metastasis cell lines in vitro. The pentapeptide Tyr-(R,S)-Aaa2-Gly-Phe-Met (18) was the most effective analogue especially against the most antitumor drug-resistant cell lines HEp-2 and SW-620. Apoptosis as a mode of cell death was confirmed in these tumor cells after exposure to pentapeptide 18.