Title:
MACROMOLECULES MODIFIED BY A PHOSPHORAMIDATE AND/OR PHOSPHONAMIDE GROUP
Document Type and Number:
WIPO Patent Application WO/2010/102997
Kind Code:
A3
Abstract:
The invention relates to a modified compound that has at least one other functional group, in particular a biomolecule or macromolecule, characterised by at least one x-fold (x≥1 ) chemoselectively incorporated phosphoramidate group of general formula (I), -NPO(OR1)(OR1'), and/or at least one x-fold (x≥1 ) chemoselectively incorporated phosphonamide group of general formula (Ia), -NPO(R1XOR1'), where R1 and R1' are selected from the group containing glycerol, polyglycerol, PEG polymers of general summation formula C2nH4n+2On+1 where n ≥ 1, Cn alkyI chains where n ≥ 1; functionalised Cn alkyI chains where n ≥ 1, aryls, heteroaryl, siIyI, lipids, fluorophores, saccharides, peptides, crown ethers, or a linker that links the aforementioned groups, and where R1 and R1' can be identical or different to/from one another.
Inventors:
HACKENBERGER CHRISTIAN (DE)
DEL SIGNORE GIUSEPPE (NL)
SERWA REMIGIUSZ (DE)
WILKENING INA (DE)
VALLEE ROBERT (DE)
DEL SIGNORE GIUSEPPE (NL)
SERWA REMIGIUSZ (DE)
WILKENING INA (DE)
VALLEE ROBERT (DE)
Application Number:
PCT/EP2010/052968
Publication Date:
March 03, 2011
Filing Date:
March 09, 2010
Export Citation:
Assignee:
UNIV BERLIN FREIE (DE)
HACKENBERGER CHRISTIAN (DE)
DEL SIGNORE GIUSEPPE (NL)
SERWA REMIGIUSZ (DE)
WILKENING INA (DE)
VALLEE ROBERT (DE)
HACKENBERGER CHRISTIAN (DE)
DEL SIGNORE GIUSEPPE (NL)
SERWA REMIGIUSZ (DE)
WILKENING INA (DE)
VALLEE ROBERT (DE)
International Classes:
A61K47/48; C07K1/13
Domestic Patent References:
| WO2008128686A1 | 2008-10-30 | |||
| WO2007110624A2 | 2007-10-04 | |||
| WO2006038184A2 | 2006-04-13 | |||
| WO2001068565A2 | 2001-09-20 |
Foreign References:
| US20080081782A1 | 2008-04-03 |
Other References:
CAMP N P ET AL: "Synthesis of stereochemically defined phosphonamidate-containing peptides: Inhibitors for the HIV-1 proteinase", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, PERGAMON, ELSEVIER SCIENCE, GB, vol. 2, no. 9, 1 September 1992 (1992-09-01), pages 1047 - 1052, XP026762688, ISSN: 0960-894X, [retrieved on 19920901], DOI: DOI:10.1016/S0960-894X(00)80616-2
MORR M ET AL: "Cyclic peptide-nucleotide hybrids (cPNH) with phosphoramidate bonds", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 55, no. 10, 5 March 1999 (1999-03-05), pages 2985 - 2996, XP004157135, ISSN: 0040-4020, DOI: DOI:10.1016/S0040-4020(99)00079-4
SIKORA D ET AL: "O-Ethyl 1-azidoalkylphosphonic acids-versatile reagents for the synthesis of protected phosphonamidate peptides", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 57, no. 8, 18 February 2001 (2001-02-18), pages 1619 - 1625, XP004317617, ISSN: 0040-4020, DOI: DOI:10.1016/S0040-4020(00)01143-1
SERWA REMIGIUSZ ET AL.: "Chemoselective Staudinger-phosphite reaction of azides for the phosphorylation of proteins", ANGEWANDTE CHEMIE (INTERNATIONAL ED. IN ENGLISH), vol. 48, no. 44, 27 July 2009 (2009-07-27), Germany, pages 8234 - 8239, XP002609595, ISSN: 1521-3773
BÖHRSCH VERENA ET AL: "Site-specific functionalisation of proteins by a Staudinger-type reaction using unsymmetrical phosphites.", CHEMICAL COMMUNICATIONS (CAMBRIDGE, ENGLAND) 14 MAY 2010 LNKD- PUBMED:20424765, vol. 46, no. 18, 14 May 2010 (2010-05-14), pages 3176 - 3178, XP002609596, ISSN: 1364-548X
MORR M ET AL: "Cyclic peptide-nucleotide hybrids (cPNH) with phosphoramidate bonds", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 55, no. 10, 5 March 1999 (1999-03-05), pages 2985 - 2996, XP004157135, ISSN: 0040-4020, DOI: DOI:10.1016/S0040-4020(99)00079-4
SIKORA D ET AL: "O-Ethyl 1-azidoalkylphosphonic acids-versatile reagents for the synthesis of protected phosphonamidate peptides", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 57, no. 8, 18 February 2001 (2001-02-18), pages 1619 - 1625, XP004317617, ISSN: 0040-4020, DOI: DOI:10.1016/S0040-4020(00)01143-1
SERWA REMIGIUSZ ET AL.: "Chemoselective Staudinger-phosphite reaction of azides for the phosphorylation of proteins", ANGEWANDTE CHEMIE (INTERNATIONAL ED. IN ENGLISH), vol. 48, no. 44, 27 July 2009 (2009-07-27), Germany, pages 8234 - 8239, XP002609595, ISSN: 1521-3773
BÖHRSCH VERENA ET AL: "Site-specific functionalisation of proteins by a Staudinger-type reaction using unsymmetrical phosphites.", CHEMICAL COMMUNICATIONS (CAMBRIDGE, ENGLAND) 14 MAY 2010 LNKD- PUBMED:20424765, vol. 46, no. 18, 14 May 2010 (2010-05-14), pages 3176 - 3178, XP002609596, ISSN: 1364-548X
Attorney, Agent or Firm:
MORAWSKI, Birgit et al. (Postfach 15 09 20, Berlin, DE)
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