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Synthesis and receptor binding affinity of carboxylate analogues of the mannose 6-phosphate recognition marker.

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(1)Synthesis and receptor binding affinity of carboxylate analogues of the mannose 6-phosphate recognition marker. Audrey Jeanjean, Marcel Garcia, Alain Leydet, Jean-Louis Montero, Alain Morère. To cite this version: Audrey Jeanjean, Marcel Garcia, Alain Leydet, Jean-Louis Montero, Alain Morère. Synthesis and receptor binding affinity of carboxylate analogues of the mannose 6-phosphate recognition marker.. Bioorganic and Medicinal Chemistry, Elsevier, 2006, 14 (10), pp.3575-82. �10.1016/j.bmc.2006.01.024�. �inserm-00144764�. HAL Id: inserm-00144764 https://www.hal.inserm.fr/inserm-00144764 Submitted on 7 May 2007. HAL is a multi-disciplinary open access archive for the deposit and dissemination of scientific research documents, whether they are published or not. The documents may come from teaching and research institutions in France or abroad, or from public or private research centers.. L’archive ouverte pluridisciplinaire HAL, est destinée au dépôt et à la diffusion de documents scientifiques de niveau recherche, publiés ou non, émanant des établissements d’enseignement et de recherche français ou étrangers, des laboratoires publics ou privés..

(2) HAL author manuscript. Bioorganic & Medicinal Chemistry / Bioorganic & Medicinal Chemistry 15/05/2006; 14(10. HAL author manuscript. 

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(84) TMSO. OTMS O. HAL author manuscript. TMSO TMSO. O. EtO.  QM?\. OTMS O. TMSO TMSO. OCH3. Y . O. NaO. inserm-00144764, version 1. HO HO. OH O. OCH3 Z.

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(96) O HO. . OBn O. HAL author manuscript. BnO BnO. OtBu. O. b ^c. OBn O. BnO BnO. OCH3. _ 4 O. ONa. O. inserm-00144764, version 1. 6& O. OH O. HO HO. a. ee c. OCH3. db c. ONa. O. OBn O. BnO BnO. `. OCH3. OCH3. 

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(109) TfO BnO BnO. . OBn O. CO2Me. NK;f. MeO2C. HAL author manuscript. OBn O. BnO BnO. OCH3. c D. CO2H. CO2Na NaO2C. inserm-00144764, version 1. HO HO. g ;f. OCH3. OH O. %D g \f. HO2C BnO BnO. OBn O. e d OCH3 OCH3 

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(124) Bound M6P/IGF2Rb (OD 450nm). inserm-00144764, version 1. Bound M6P/IGF2Rb (OD 450nm). HAL author manuscript. A. B. 1,2. 0,6. 0,8. 0,3. 0. 100 200 PMP (µg.mL-1). 0,4. 0. 1 2 3 4 -1 M6P/IGF2Rb (µg.mL ). 5. Œ a\ ®FH@I ™ nI&cdIKHzM\aPO?c\eh0PMhTš

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(129) B. inserm-00144764, version 1. Bound M6P/IGF2Rb (OD 450 nm). HAL author manuscript. Bound M6P/IGF2Rb (OD 450 nm). A. 0,8. 0,4 Unsaturated 2 Saturated 3 non isosteric 6 0. 0,8. 0,4. 10-8 10 -7 10 -6 10 -5 10 -4 10-3. M6P PMP Malonate 0. Analogues (M). -8. 10. -7. 10. -3 10-6 10-5 10-4 10. Analogues (M).  \]jd€Y`ORXIz„IfPRckhTš2²WB²Åš H@hTz»WC‘l²¬ @Z Œ T‰Ii[vTJoWC‘l²ÇOfPOYah0®F*IjN™ Œ \a®FH@I™ . j@yh¯„j6c'yTO=c¼W‡‘l²Ì€TH.Ilj@IKPRc@jµ@x Œ V\ H=j–c>OKPOfYaJ

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