Process for the preparation of azidoperfluoroalkanes and azidopolyfluoroalkanes of general formula R.sub.FN.sub.3, where R.sub.F is chosen from a group containing C.sub.nF.sub.2n+1, C.sub.nF.sub.xH.sub.2n+1x, C.sub.nF.sub.xX.sub.2n+1x or R.sup.1CF.sub.2CF.sub.2, where n is an integer in the range of 1 to 10, x is an integer in the range of 2 to 20, X is Cl, Br, or I, R.sup.1 is C.sub.1-10 alkyl, ArO, ArS, imidazolyl, benzimidazolyl, or pyrazolyl and Ar is phenyl or substituted phenyl, by the reaction of electrophilic azidation reagent of general formula R.sup.2N.sub.3, where R.sup.2 is n-C.sub.4F.sub.9SO.sub.2, ArSO.sub.2, Br, I, with synthetic equivalent of polyfluoroalkylated carbanion of general formula [R.sub.F].sup..

Process for the preparation of azidoperfluoroalkanes and azidopolyfluoroalkanes of general formula R.sub.FN.sub.3, where R.sub.F is chosen from a group containing C.sub.nF.sub.2n+1, C.sub.nF.sub.xH.sub.2n+1x, C.sub.nF.sub.xX.sub.2n+1x or R.sup.1CF.sub.2CF.sub.2, where n is an integer in the range of 1 to 10, x is an integer in the range of 2 to 20, X is Cl, Br, or I, R.sup.1 is C.sub.1-10 alkyl, ArO, ArS, imidazolyl, benzimidazolyl, or pyrazolyl and Ar is phenyl or substituted phenyl, by the reaction of electrophilic azidation reagent of general formula R.sup.2N.sub.3, where R.sup.2 is n-C.sub.4F.sub.9SO.sub.2, ArSO.sub.2, Br, I, with synthetic equivalent of polyfluoroalkylated carbanion of general formula [R.sub.F].sup..

Provided herein are methods and compositions for oligonucleotide synthesis utilizing universal linker phosphoramidites. Methods and reagents are described with DNA synthesis using controlled pore glass (CPG) solid supports, and on platinum coated electrodes for electrochemical DNA synthesis. The universal linkers can be used as spacers in single-column PCR primer synthesis to generate 2 strands with free 3-hydroxy termini after cleavage. The methods and compositions utilize a solid support system for synthesis of oligonucleotides, wherein the support has platinum electrodes and a universal linker, optionally wherein the platinum electrode is coated with an amine. The methods and compositions further describe use of universal linker phosphoramidites and the platinum electrode is coated with a monosaccharide, or a disaccharide.

Provided herein are methods and compositions for oligonucleotide synthesis utilizing universal linker phosphoramidites. Methods and reagents are described with DNA synthesis using controlled pore glass (CPG) solid supports, and on platinum coated electrodes for electrochemical DNA synthesis. The universal linkers can be used as spacers in single-column PCR primer synthesis to generate 2 strands with free 3-hydroxy termini after cleavage. The methods and compositions utilize a solid support system for synthesis of oligonucleotides, wherein the support has platinum electrodes and a universal linker, optionally wherein the platinum electrode is coated with an amine. The methods and compositions further describe use of universal linker phosphoramidites and the platinum electrode is coated with a monosaccharide, or a disaccharide.

Nitrogen containing compounds may have formulas (I), (II) and (IV), and such compounds may be suitable for detecting alkyne group containing organic compounds by mass spectrometry. Furthermore, methods may also include synthesizing these compounds, detecting of organic compounds containing the specific compounds, uses of the compounds in mass spectrometry for determining enzyme activity or monitoring the lipid metabolism in a cell, and a kit which contains at least one of these compounds and at least one internal standard.

Nitrogen containing compounds may have formulas (I), (II) and (IV), and such compounds may be suitable for detecting alkyne group containing organic compounds by mass spectrometry. Furthermore, methods may also include synthesizing these compounds, detecting of organic compounds containing the specific compounds, uses of the compounds in mass spectrometry for determining enzyme activity or monitoring the lipid metabolism in a cell, and a kit which contains at least one of these compounds and at least one internal standard.

A PEG linker as represented by formula (I), wherein n and m are respectively an integer from 1 to 7, providing the PEG linker with 1 to 49 linking sites. A ligand drug conjugate as represented by formula (II). The conjugate uses the PEG linker to increase a drug loading capacity and drug loading diversity, thereby improving pharmaceutical efficacy.

Y1-PEG1-{R.sup.1-PEG2-{Y4}.sub.n}.sub.m(I)

TM-{R.sup.2-PEG1-{R.sup.1-PEG2-{R.sup.3-A-drug}.sub.n}.sub.m}.sub.l(II)

A PEG linker as represented by formula (I), wherein n and m are respectively an integer from 1 to 7, providing the PEG linker with 1 to 49 linking sites. A ligand drug conjugate as represented by formula (II). The conjugate uses the PEG linker to increase a drug loading capacity and drug loading diversity, thereby improving pharmaceutical efficacy.

Y1-PEG1-{R.sup.1-PEG2-{Y4}.sub.n}.sub.m(I)

TM-{R.sup.2-PEG1-{R.sup.1-PEG2-{R.sup.3-A-drug}.sub.n}.sub.m}.sub.l(II)

The present invention relates to a cycloaddition process comprising the step of reacting a halogenated aliphatic 1,3-dipole compound with a (hetero)cycloalkyne according to Formula (1): Preferably, the (hetero)cycloalkyne according to Formula (1) is a (hetero)cyclooctyne. The invention also relates to the cycloaddition products obtainable by the process according to the invention. The invention further relates to halogenated aliphatic 1,3-dipole compounds, in particular to halogenated aliphatic 1,3-dipole compounds comprising N-acetylgalactosamine-UDP (GalNAc-UDP), and to halogenated 1,3-dipole compounds comprising (peracylated) N-acetylglucosamine (GlcNAc), N-acetylgalactosamine (GalNAc), N-acetylmannosamine (ManNAc) and N-acetyl neuraminic acid (NeuNAc). ##STR00001##

The present invention relates to a cycloaddition process comprising the step of reacting a halogenated aliphatic 1,3-dipole compound with a (hetero)cycloalkyne according to Formula (1): Preferably, the (hetero)cycloalkyne according to Formula (1) is a (hetero)cyclooctyne. The invention also relates to the cycloaddition products obtainable by the process according to the invention. The invention further relates to halogenated aliphatic 1,3-dipole compounds, in particular to halogenated aliphatic 1,3-dipole compounds comprising N-acetylgalactosamine-UDP (GalNAc-UDP), and to halogenated 1,3-dipole compounds comprising (peracylated) N-acetylglucosamine (GlcNAc), N-acetylgalactosamine (GalNAc), N-acetylmannosamine (ManNAc) and N-acetyl neuraminic acid (NeuNAc). ##STR00001##