Synthesis of coumarin or ferrocene labeled nucleosides via Staudinger ligation

• Ivana Kosiova,
• Andrea Janicova and
• Pavol Kois

Beilstein J. Org. Chem. 2006, 2, No. 23, doi:10.1186/1860-5397-2-23

• gives iminophosphoranes which can react with almost any kind of electrophilic reagent, e.g. aldehydes/ketones to form imines or esters to form amides. This so-called Staudinger ligation has been employed in a wide range of applications as a general tool for bioconjugation including specific labeling of

• , [22][23] including specific labeling of nucleic acids, [24] proteomic studies [25][26] and modification of cell surfaces. [17][18] We applied the Staudinger ligation for nucleoside labeling procedures, using coumarin and ferrocene derivatives as labels. According to our knowledge, applications of this

• with maxima of 1a-c. We observed only slight changes of fluorescence intensity in the series of coumarin labeled nucleosides. We also tested the Staudinger ligation as a prospective method for the electrochemical labeling of nucleosides and nucleotides with ferrocene derivatives. 2'-Azido-2

Molecular recognition. 1. Crystal structures of hexaazamacrocyclic amines containing p-xylylene spacers and their adducts with acids

• Teresa Borowiak,
• Grzegorz Dutkiewicz,
• Maciej Kubicki,
• Marek Pietraszkiewicz,
• Agnieszka Gil and
• Rainer Mattes

Beilstein J. Org. Chem. 2005, 1, No. 16, doi:10.1186/1860-5397-1-16

• isolated centrosymmetric molecules. The molecular conformation together with the atom labeling scheme is shown in Figure 4. The overall conformation of the molecule is ellipsoidal with the approximate dimensions of 6.2 and 15.3 Å. All atoms of the molecule (except hydrogens) are within 2.16 Å of the mean

• from one macrocyclic hexa-protonated cation and six fumaric anions, together with the atom labeling scheme. Displacement parameters are drawn at 50% probability level. Symmetry codes: i: 0.5-x, 0.5+y, z; ii: 0.5-x, 0.5+y, 0.5-z; iii 0.5-x, -0.5+y, z; iv: 0.5-x, -0.5+y, 0.5-z The structure of one sheet

• height of one sheet corresponds to the height of the macrocycle, i.e. about 12 Å. The molecular conformation of 1-N-Me, atom labeling scheme indicated. Displacement parameters are drawn at 50% probability level. The unit cell of 1-N-Me, stacks of molecules are indicated. Formulas of macrocyclic amines, 1