95853-35-3

Basic information

• Product Name: (2S)-(3R,5S)-Adamantan-1-yl(amino)acetic acid
• Synonyms: (2S)-(3R,5S)-Adamantan-1-yl(amino)essigs?ure;Tricyclo[3.3.1.13,7]decane-1-acetic acid, α-amino-, (αS)-
• CAS NO: 95853-35-3
• Molecular Formula: C12H19NO2
• Molecular Weight: 209.288
• Mol File: 95853-35-3.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (2S)-(3R,5S)-Adamantan-1-yl(amino)acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-(3R,5S)-Adamantan-1-yl(amino)acetic acid(95853-35-3)
• EPA Substance Registry System: (2S)-(3R,5S)-Adamantan-1-yl(amino)acetic acid(95853-35-3)

Safety Data

• Hazardous Substances Data: 95853-35-3(Hazardous Substances Data)

Upstream product

• 1373751-77-9 D-(adamant-1-yl)glycyl-L-alanyl-D-isoglutamine 
• 328969-77-3 (S)-N-(benzyloxycarbonyl)-2-(1-adamantyl)-2-aminoethanol 
• 895167-07-4 adamantan-1-yl-[2-tert-butoxycarbonylamino-3-(4-tert-butoxycarbonyloxy-phenyl)-propionylamino]-acetic acid 
• 895166-80-0 (R)-Adamantan-1-yl-[(S)-2-amino-3-(4-hydroxy-phenyl)-propionylamino]-acetic acid 
• 102572-74-7 R-methyl ester of amino-(1-adamantanyl)acetic acid 
• 2094-72-6 1-Adamantanecarbonyl chloride 
• 16091-97-7 1-adamantyl-2-hydroxyiminoacetic acid 
• 828-51-3 1-Adamantanecarboxylic acid 
• 16091-98-8 oxo-tricyclo[3.3.1.1^3,7]decan-1-yl-acetic acid 
• 1660-04-4 1-acetyladamantane 
• 98398-64-2 Adamantan-1-yl-iodo-acetyl chloride 
• 98398-65-3 2-bromoadamantaneacetyl chloride 
• 82650-30-4 adamantan-1-yliodoacetic acid 
• 59768-70-6 2-(1-adamantyl)-2-bromoacetic acid 

Downstream Products

• 709031-29-8 3-hydroxy-1-adamantyl-glycine 
• 361442-00-4 (αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.1^3,7]decane-1-acetic acid 
• 709031-29-8 (αS)-α-amino-3-hydroxytricyclo[3.3.1.1^3,7]decane-1-acetic acid 
• 328969-74-0 rac-N-(benzyloxycarbonyl)-2-(1-adamantyl)-2-aminoethanol 
• 361442-01-5 tert-butyl [(1S)-2-[(1S,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hex-2-yl]-1-(3-hydroxytricyclo[3.3.1.1³'⁷]dec-1-yl)-2-oxoethyl]carbamate 
• 709031-43-6 3-cyano-(αS)-α-(3-hydroxytricyclo[3.3.1.1^3,7]dec-1-yl)-β-oxo-(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-2-ethanecarbamic acid 1,1-dimethylethyl ester 
• 681282-72-4 (S)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dihydroxyadamantan-1-yl)acetic acid 
• 361441-97-6 (alpha S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]tricyclo[3.3.1.1^3,7]decane-1-acetic acid 

Relevant articles and documents

Adamantylation of hydantoin

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Synthesis and immunostimulating properties of novel adamant-1-yl tripeptides

The aim of this work was to prepare L- and D-(adamant-1-yl)-Gly-L-Ala-D- isoGln peptides in order to study their adjuvant (immunostimulating) activities. Adjuvant activity of adamant-1-yl tripeptides was tested in the mouse model using ovalbumin as an ant

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.