276241-97-5

Basic information

• Product Name: (7S,12S,18S,23S)-Dimethyl 12,18-dibenzyl-7,23-bis(tert-butoxycarbonylamino)-6,10,13,17,20,24-hexaoxo-5,11,14,16,19,25-hexaaza-15(2,6)-pyridina-1,29⁽¹⁾,3,27(1,4)-tetrabenzenanonacosaphane-1⁴,29⁴-dicarboxylate
• Synonyms: (7S,12S,18S,23S)-Dimethyl 12,18-dibenzyl-7,23-bis(tert-butoxycarbonylamino)-6,10,13,17,20,24-hexaoxo-5,11,14,16,19,25-hexaaza-15(2,6)-pyridina-1,29⁽¹⁾,3,27(1,4)-tetrabenzenanonacosaphane-1⁴,29⁴-dicarboxylate
• CAS NO: 276241-97-5
• Molecular Weight: 1336.55
• Mol File: 276241-97-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (7S,12S,18S,23S)-Dimethyl 12,18-dibenzyl-7,23-bis(tert-butoxycarbonylamino)-6,10,13,17,20,24-hexaoxo-5,11,14,16,19,25-hexaaza-15(2,6)-pyridina-1,29⁽¹⁾,3,27(1,4)-tetrabenzenanonacosaphane-1⁴,29⁴-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (7S,12S,18S,23S)-Dimethyl 12,18-dibenzyl-7,23-bis(tert-butoxycarbonylamino)-6,10,13,17,20,24-hexaoxo-5,11,14,16,19,25-hexaaza-15(2,6)-pyridina-1,29⁽¹⁾,3,27(1,4)-tetrabenzenanonacosaphane-1⁴,29⁴-dicarboxylate(276241-97-5)
• EPA Substance Registry System: (7S,12S,18S,23S)-Dimethyl 12,18-dibenzyl-7,23-bis(tert-butoxycarbonylamino)-6,10,13,17,20,24-hexaoxo-5,11,14,16,19,25-hexaaza-15(2,6)-pyridina-1,29⁽¹⁾,3,27(1,4)-tetrabenzenanonacosaphane-1⁴,29⁴-dicarboxylate(276241-97-5)

Safety Data

• Hazardous Substances Data: 276241-97-5(Hazardous Substances Data)

Upstream product

• 276241-95-3 9-Allyl 1-methyl (7S)-7-(tert-butoxycarbonylamino)-6-oxo-5-aza-1⁽¹⁾,3(1,4)-dibenzenanonaphane-1⁴,9-dicarboxylate 
• 276241-94-2 (1S,7S)-1,7-Dibenzyl-1,7-bis(tert-butoxycarbonylamino)-3,5-diaza-4(2,6)-pyridinaheptaphane-2,6-dione 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 141-86-6 2.6-diaminopyridine 
• 276241-96-4 (7S)-1⁴-Methoxycarbonyl-7-tert-butoxycarbonylamino-6-oxo-5-aza-1⁽¹⁾,3(1,4)-dibenzenanonaphane-9-carboxylic acid 
• 132286-79-4 N-α-(t-butoxycarbonyl)-L-glutamic γ-allyl ester 

Relevant articles and documents

Synthesis and binding properties of a macrobicyclic receptor for N-protected peptides with a carboxylic acid terminus

A novel macrobicyclic receptor, 3, has been synthesised by linking together a diaminopyridine with suitable amino acids, followed by a double intramolecular cyclisation of a suitably activated precursor. Macrobicycle 3 features a diamidopyridirie unit, designed to serve as a specific binding site for carboxylic acid functionality, at the base of an open, bowl-shaped cavity. Incorporation of additional amide functionality around the rim of the bowl-shaped structure provides further hydrogen bonding sites to interact with pcptidic guests. The binding properties of 3 with N-protected amino acid and peptide derivatives have been investigated by NMR titration experiments, which reveal that 3 is a strong and selective receptor for peptides with a carboxylic acid terminus in CDCl3 solution, the strongest binding being observed with Cbz-β-alanyl-D-alanine (-ΔGass = 22.8 kJ mol-1). The macrobicycle is reasonably enantioselective (Cbz-β-alanyl-L-alanine, -ΔGass = 19.1 kJ mol-1) and notably the binding of Cbz-β-alanyl lactic acids is considerably weaker than the binding of the corresponding Cbz-β-alanyl alanines (ΔΔGass ～ 8-9 kJ mol-1). Molecular modelling and 2D NMR studies have been carried out on the free macrobicycle and the 1:1 complex formed with the most strongly bound substrate (Cbz-β-alanyl-D-alanine). These studies provide a consistent picture of the macrobicycle as a flexible receptor, which is able to bind the Cbz-β-alanyl-D-alanine substrate in the macrobicyclic cavity with a series of well defined hydrogen bonds to the alanylalanine amide, and less well defined hydrogen bonds to the benzylcarbamate functionality. The Royal Society of Chemistry 2000.