Supporting Information. Synthesis of heteroglycoclusters by using orthogonal
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1 Supporting Information for Synthesis of heteroglycoclusters by using orthogonal chemoselective ligations Baptiste Thomas 1, Michele Fiore 1, Isabelle Bossu 1, Pascal Dumy 1 and Olivier Renaudet* 1,2 Address: 1 Département de Chimie Moléculaire, UMR-CNRS 5250 & ICMG FR 2607, Université Joseph Fourier, PB 53, Grenoble Cedex 9, France and 2 Institut Universitaire de France, 103 boulevard Saint-Michel, Paris, France. Olivier Renaudet* - olivier.renaudet@ujf-grenoble.fr *Corresponding author Crude RP-HPLC profiles and ESI-MS spectra for the heteroglycoclusters Table of contents: 1. Analytical data for compound 5-Man S3 2. Analytical data for compound 5-Fuc S4 3. Analytical data for compound 5-Lac S5 4. Analytical data for compound 6-Man/Fuc S6 5. Analytical data for compound 6-Man/Lac S7 6. Analytical data for compound 6-Fuc/Man S8 S9 7. Analytical data for compound 6-Fuc/Lac S10 8. Analytical data for compound 6-Lac/Man S11 S1
2 9. Analytical data for compound 6-Lac/Fuc S Analytical data for compound 7-Man S Analytical data for compound 7-Fuc S Analytical data for compound 7-Lac S Analytical data for compound 8-Man/Fuc S Analytical data for compound 8-Man/Lac S Analytical data for compound 8-Fuc/Man S18 S Analytical data for compound 8-Fuc/Lac S Analytical data for compound 8-Lac/Man S Analytical data for compound 8-Lac/Fuc S22 General details All chemical reagents were purchased from Aldrich (Saint Quentin Fallavier, France) or Acros (Noisy-Le-Grand, France) and were used without further purification. Protected amino acids and Fmoc-Gly-Sasrin resin were obtained from Advanced ChemTech Europe (Brussels, Belgium), Bachem Biochimie SARL (Voisins-Les-Bretonneux, France) and France Biochem S.A. (Meudon, France). PyBOP was purchased from France Biochem. Reaction progress was monitored by reverse-phase HPLC on Waters equipment by using C 18 columns. Analytical and preparative separation was carried out at 1.0 ml/min (EC 125/3 nucleosil C 18 ) and at 22 ml/min (VP 250/21 nucleosil C 18 ) with UV monitoring at 214 nm and 250 nm by using a linear A B gradient (buffer A: 0.09% CF 3 CO 2 H in water; buffer B: 0.09% CF 3 CO 2 H in 90% acetonitrile). Each glycopeptide was analyzed by mass spectrometry by using electrospray ionization on an Esquire Bruker Daltonics in positive mode. 1 H NMR and G-COSY were recorded in D 2 O at 400 MHz with a Bruker Avance 400 spectrometer. S2
3 1. Analytical data for compound 5-Man ESI-MS (positive mode): calcd for C 60 H 97 N 20 O , found: m/z [M + H] + S3
4 2. Analytical data for compound 5-Fuc ESI-MS (positive mode): calcd for C 60 H 96 N 20 O 22 Na , found: m/z [M + Na] + S4
5 3. Analytical data for compound 5-Lac ESI-MS (positive mode): calcd for C 72 H 117 N 20 O , found: m/z [M + H] + S5
6 4. Analytical data for compound 6-Man/Fuc ESI-MS (positive mode): calcd for C 78 H 124 N 20 O , found: m/z [M + H] + S6
7 5. Analytical data for compound 6-Man/Lac ESI-MS (positive mode): calcd for C 90 H 144 N 20 O , found: m/z [M + H] + S7
8 6. Analytical data for compound 6-Fuc/Man ESI-MS (positive mode): calcd for C 78 H 124 N 20 O , found: m/z [M + H] + S8
9 1 H NMR (D 2 O, 400 MHz) ppm (t1) G-COSY (D 2 O, 400 MHz) 8.0 ppm (t2) S9
10 7. Analytical data for compound 6-Fuc/Lac ESI-MS (positive mode): calcd for C 90 H 144 N 20 O , found: m/z [M + H] + S10
11 8. Analytical data for compound 6-Lac/Man ESI-MS (positive mode): calcd for C 90 H 145 N 20 O , found: m/z [M + H] + S11
12 9. Analytical data for compound 6-Lac/Fuc ESI-MS (positive mode): calcd for C 90 H 145 N 20 O , found: m/z [M + H] + S12
13 10. Analytical data for compound 7-Man ESI-MS (positive mode): calcd for C 52 H 84 N 21 O , found: m/z [M + H] + S13
14 11. Analytical data for compound 7-Fuc ESI-MS (positive mode): calcd for C 52 H 84 N 21 O , found: m/z [M + H] + S14
15 12. Analytical data for compound 7-Lac ESI-MS (positive mode): calcd for C 58 H 94 N 21 O , found: m/z [M + H] + S15
16 13. Analytical data for compound 8-Man/Fuc ESI-MS (positive mode): calcd for C 79 H 126 N 21 O , found: m/z [M + H] + S16
17 14. Analytical data for compound 8-Man/Lac ESI-MS (positive mode): calcd for C 97 H 156 N 21 O , found: m/z [M + H] + S17
18 15. Analytical data for compound 8-Fuc/Man ESI-MS (positive mode): calcd for C 79 H 126 N 21 O , found: m/z [M + H] + S18
19 1 H NMR (D 2 O, 400 MHz) ppm (t1) G-COSY (D 2 O, 400 MHz) 8.0 ppm (t2) S19
20 16. Analytical data for compound 8-Fuc/Lac ESI-MS (positive mode): calcd for C 97 H 156 N 21 O , found: m/z [M + H] + S20
21 17. Analytical data for compound 8-Lac/Man ESI-MS (positive mode): calcd for C 85 H 136 N 21 O , found: m/z [M + H] + S21
22 18. Analytical data for compound 8-Lac/Fuc ESI-MS (positive mode): calcd for C 85 H 136 N 21 O , found: m/z [M + H] + S22
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