1,8-Diamino-3,6-dioxaoCtane - CAS 929-59-9

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Catalog Number
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Molecular Weight
Molecular Formula
CAS 929-59-9 1,8-Diamino-3,6-dioxaoCtane
Boiling Point
105-109ºC (6 mmHg)
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Reference Reading
1.DOTTADs--readily made novel metal ligands with multivariant functionality.
Arany A1, Meth-Cohn O, Nyerges M. Org Biomol Chem. 2003 May 7;1(9):1545-51.
The interaction of Hantzsch pyridinecarboxylic acids with dialkylformamides and POCl3, followed by treatment with NH4OH yields 1,8-dioxo-1,2,7,8-tetrahydro-2,7,10-triazaanthracenes (DOTTADs), which have great potential as useful ligands for Group I and II metals and some transition metals. The corresponding Hantszch esters similarly for DOTTADs or their bis-imines by way of isolable intermediates, which are then treated with an amine RNH2. DOTTAD-imines are also available from DOTTADs with amines and this reaction is also effective with 1,8-diamino-3,6-dioxaoctane to give macrocyclic analogues, as well as with chiral amines. DOTTAD-imines can be reduced with diethylsilane and Wilkinson's catalyst to the corresponding amines, which can also be formed from DOTTADs by reductive amination with amines and Na(AcO)3BH. Mono-aldols of DOTTADs are easily formed by treatment of DOTTADs with acetone.
2.Use of microbial transglutaminase for the enzymatic biotinylation of antibodies.
Josten A1, Haalck L, Spener F, Meusel M. J Immunol Methods. 2000 Jun 23;240(1-2):47-54.
Nowadays many reagents are available for the biotinylation of proteins. As most of them bind to amino groups of the protein the degree of labelling differs from batch to batch and the possibility exists that the biological activity of the target protein may be affected by the labelling procedure. In the present study we have investigated an enzymatic approach to biotinylation using microbial transglutaminase (MTGase) from Streptoverticillium mobaraense. The proposed method is particularly suitable when only a few biotin molecules need to be attached to the target proteins. The enzyme catalyses the acyl transfer reaction between gamma-carboxyamide groups and various primary amines. This was exploited for biotinylation using two amino-modified biotin derivatives, biotinamido-5-pentylamin (BIAPA) and biotinoyl-1,8-diamino-3, 6-dioxaoctane (BIDADOO) as acyl acceptors and a monoclonal IgG against the herbicide 2,4-dichlorophenoxyacetic acid (2,4-D) as the acyl donor.
3.Synthesis, characterization, and catalytic properties of cationic hydrogels containing copper(II) and cobalt(II) ions.
Lombardo Lupano LV1, Lázaro Martínez JM, Piehl LL, Rubín de Celis E, Torres Sánchez RM, Campo Dall' Orto V. Langmuir. 2014 Mar 18;30(10):2903-13. doi: 10.1021/la404799t. Epub 2014 Mar 7.
Here, we report the synthesis and characterization of a hydrogel based on ethylene glycol diglycidyl ether (EGDE) and 1,8-diamino-3,6-dioxaoctane (DA). Chemically stable Co(II) and Cu(II) coordination complexes were prepared with this nonsoluble polyelectrolyte, poly(EGDE-DA), and studied by ss-NMR, FT-IR, thermogravimetry, and microscopy. Mesopores were found in all the samples, the thermal stability of the polymer matrix was highly affected by the presence of metal ions, and the (13)C CP-MAS spectrum for the Cu(II)-complex evidenced a significant increase in the reticulation degree by Cu(II) ions. The catalytic activity of these materials on H2O2 activation was studied by electron spin resonance (ESR). The Co(II)-poly(EGDE-DA)/H2O2 heterogeneous system produced O2, an anion superoxide (O2(•)¯), and a hydroxyl radical (OH(•)), which diffused into the solution at the time that a decrease in pH was detected. In the same way, the Cu(II)-poly(EGDE-DA)/H2O2 heterogeneous system produced O2 and OH(•).
4.A non-isotopic immunoassay for guanosine 3':5'-cyclic monophosphate using a cyclic GMP-biotin conjugate as tracer.
Dressendörfer RA1, Heim JM, Gerzer R, Strasburger CJ. J Immunoassay. 1995 Feb;16(1):37-53.
2'-O-monosuccinylguanosine 3':5'-cyclic monophosphate was coupled to N-biotinyl-1,8-diamino-3,6-dioxaoctane after converting succinyl-cGMP into its N-hydroxysuccinimide active ester. Isolation and purification of the succinyl-cGMP-biotin conjugate was performed with FPLC using reversed phase chromatography. The synthesis described yielded a conjugate suitable for use as tracer in immunoassays for the cGMP measurement in plasma and urine samples. Employing biotin as the primary probe in a competitive solid phase immunoassay allows for flexible end point determination by means of commercially available labeled streptavidin derivatives. Streptavidin-europium was used in conjunction with the DELFIA-system for time-resolved fluorometric end point measurement (TR-FIA), streptavidin-horseradish peroxidase was used for colorimetric end point determination (EIA). Both non radioactive immunoassay systems showed excellent correlation with the reference radioimmunoassay, good sensitivity and reproducibility.
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