Solid Phase Peptide Synthesis (SPPS) and Solid Phase. Fragment Coupling (SPFC) Mediated by Isonitriles

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1 Solid Phase Peptide Synthesis (SPPS) and Solid Phase Fragment Coupling (SPFC) Mediated by Isonitriles Ting Wang a and Samuel J. Danishefsky a,b,* alaboratory for Bioorganic Chemistry, Sloan- Kettering Institute for Cancer Research, 1275 York Avenue, ew York, Y 165 bdepartment of Chemistry, Columbia University, avemeyer all, 3 Broadway, ew York, Y 127 SUPPRTIG IFRMATI General Information. All commercial materials (Aldrich, Alfa Aesar, ovabiochem) were used without further purification. All solvents were reagent grade or PLC grade (Fisher, Aldrich). Anhydrous TF, C2Cl2 were passed through column of alumina and used without further drying. 1 MR spectra and 13 C MR spectra were recorded on a Bruker Advance DRX- 6 Mz at ambient temperature unless otherwise stated. Chemical shifts were reported in parts per million relative to residual solvent CDCl3 ( 1, 7.26 ppm, 13 C, 77. ppm). Multiplicities were reported as follows: s= singlet, d= doublet, t= triplet, m= multiplet, app.= apparent, br s= broad singlet. All 13 C MR spectra were recorded with complete proton decoupling. Low- resolution mass spectral analyses were performed with a JEL JMS- DX- 33- F mass spectrometer or Waters Micromass ZQ mass spectrometer. All reactions were carried out in oven- dried glassware under an argon or nitrogen atmosphere unless otherwise noted. Analytical TLC were performed on E. Merck silica gel 6 F254 plates and visualized by UV fluorescence quenching and CAM staining. Flash column

2 chromatography was performed on E. Merck silica get 6 (4-63mm). Yields refer to chromatographically and spectroscopically pure compounds. PLC: All separations of peptides involved a mobile phase of.5 TFA (v/v) in water (solvent A)/.4 TFA in acetonitrile (solvent B). Preparative and analytical PLC separation was performed using a Rainin PXL solvent delivery system equipped with a Rainin UV- 1 detector. LC- MS chromatographic separations were performed using a Waters Acquity Ultra Performance LC system equipped with acquity UPLC BE C18 column (1.7 µm, mm) at a flow rate of.3 ml/min, X-Terra TM MS C18 column (3.5 µm, mm) or Varain Microsorb C18 column (2 15. mm) at a flow rate of.2 ml/min. PLC separations were performed using: X-Bridge TM Prep C18 column BDTM (5. µm, mm) at a flow rate of 16 ml/min, Microsorb 1-5 C18 column at a flow rate of 16. ml/min.

3 General procedure for isonitrile mediated amidation X R 1 R 2 Fmoc To a suspension of solid support amino acid 8 (.21 mmol) in DMF (1 ml) was added Fmoc- Asn(Trt)- S 9 (.315 mmol), Bt(4.3 mg,.315 mmol) followed by t- BuC(3.56 μl,.315 mmol). The reaction mixture was shaken at ambient temperature 3-15 hours. The resin was then washed sequentially with C2Cl2/Me (1:1, v/v, 3 1 ml), DMF (3 1 ml) and Me (3 1 ml), dried by a stream of 2 and put on high vacuum overnight. The resin cleavage was then executed by treatment with TFA/TIPS/2 (9.5 ml/.25 ml/.25 ml) for 9 min. After removal of TFA by evaporation with a stream of 2, the residue was washed by cold ether, dissolved in C3C/2 (1:1, 1 ml) and lyophilized to yield peptide 1 in good purity.

4 2 Fmoc 2 1 C18, 1-5 TW : Range: C18, 1-5 TW (4.719) Cm (911:913) e e Figure S- 1. (Left) UV trace from UPLC- MS analysis of dipeptide 1; retention time = 4.68 min, gradient 1-5 C3C/2 with.5 TFA over 6 min at a flow rate of.3 ml/min, C18 column. (Right) ESI- MS of 1. LRMS (ESI+) calcd. for C [(M+) + ]: 483.2, found:

5 Fmoc 2 12 C18, 3-6 TW : Range: 2.176e+2 C18, 3-6 TW (4.511) Cm (656:668) e7 2.e+2 1.8e+2 1.6e+2 1.4e+2 1.2e+2 1.e+2 8.e+1 6.e+1 4.e e Figure S- 2. (Left) UV trace from UPLC- MS analysis of dipeptide 12; retention time = 4.48 min, gradient 3-6 C3C/2 with.5 TFA over 6 min at a flow rate of.3 ml/min, C18 column. (Right) ESI- MS of 12. LRMS (ESI+) calcd. for C [(M+) + ]: 482.2, found:

6 2 15 Fmoc C18, 1-5 TW : Range: 1.684e+2 C18, 1-5 TW (3.73) Cm (534:548) e7 1.6e+2 1.5e+2 1.4e+2 1.3e+2 1.2e+2 1.1e+2 1.e+2 9.e+1 8.e+1 7.e+1 6.e+1 5.e+1 4.e+1 3.e+1 2.e+1 1.e Figure S- 3. (Left) UV trace from UPLC- MS analysis of dipeptide 15; retention time = 3.65 min, gradient 1-5 C3C/2 with.5 TFA over 6 min at a flow rate of.3 ml/min, C18 column. (Right) ESI- MS of 15. LRMS (ESI+) calcd. for C24356 [(M+) + ]: 484.2, found:

7 17 Fmoc C18, 4-8 TW : Range: 1.585e+2 C18, 4-8 TW (3.533) Cm (688:73) e7 1.5e+2 1.4e+2 1.3e+2 1.2e+2 1.1e+2 1.e+2 9.e+1 8.e+1 7.e+1 6.e+1 5.e+1 4.e+1 3.e+1 2.e+1 1.e Figure S- 4. (Left) UV trace from UPLC- MS analysis of dipeptide 17; retention time = 3.47 min, gradient 4-8 C3C/2 with.5 TFA over 6 min at a flow rate of.3 ml/min, C18 column. (Right) ESI- MS of 17. LRMS (ESI+) calcd. for C [(M+) + ]: 411.2, found:

8 2 SSt-Bu 2 2 Fmoc C18, 4-6 TW :41 Range: 8.272e+1 C18, 4-6 TW (3.455) Cm (499:519) e7 8.e+1 7.5e+1 7.e+1 6.5e+1 6.e+1 5.5e+1 5.e+1 4.5e+1 4.e+1 3.5e+1 3.e+1 2.5e+1 2.e+1 1.5e+1 1.e Figure S- 5. (Left) UV trace from UPLC- MS analysis of dipeptide 2; retention time = 3.4 min, gradient 4-6 C3C/2 with.5 TFA over 6 min at a flow rate of.3 ml/min, C18 column. (Right) ESI- MS of 2. LRMS (ESI+) calcd. for C354986S2 [(M+) + ]: 741.3, found:

9 General procedure for isonitrile/bt- mediated SPPS To a suspension of solid support amino acid (.2 mmol) was added piperidine/dmf solution (1:4, v/v, 2 ml). The mixture was allowed to shake for 3 min before the solution was drained away. Another portion of piperidine/dmf solution (1:4, v/v, 2 ml) was added and the mixture was allowed to shake for 7 min. After drain away the DMF solution, the resin was then washed sequentially with C2Cl2/Me (1:1, v/v, 3 1 ml), DMF (3 1 ml) and Me (3 1 ml), dried by a stream of 2. To the resulting solid support amino acid/peptide was added DMF (1 ml), Fmoc- XXX- S (.3 mmol), Bt(4.1 mg,.3 mmol) followed by t- BuC (3.4 μl,.3 mmol). The reaction mixture was shaken at ambient temperature 3-15 hours. The resin was then washed sequentially with C2Cl2/Me (1:1, v/v, 3 1 ml), DMF (3 1 ml) and Me (3 1 ml), dried by a stream of 2. The resin cleavage of peptide product was executed by treatment of with TFA/TIPS/2 (9.5 ml/.25 ml/.25 ml) for 9 min. After removal of TFA by evaporation with a stream of 2, the residue was washed by cold ether, dissolved in C3C/2 (1:1, 1 ml) and lyophilized to yield peptide, which was then purified by PLC.

10 21 Fmoc The product was purified by reversed- phase PLC (C18 column, gradient 38-78, C3C/2 with.5 TFA over 17 min). The fractions were collected and lyophilized to give 21 (8.63 mg, 17 µmol) as a white solid. C18, 4-8 TW-5-PLG-3 1: Range: 2.281e+2 C18, 4-8 TW-5-PLG (3.347) Cm (486:499) e7 2.2e+2 2.e+2 1.8e+2 1.6e+2 1.4e+2 1.2e+2 1.e+2 8.e+1 6.e+1 4.e+1 2.e Figure S- 6. (Left) UV trace from UPLC- MS analysis of purified dipeptide 21; retention time = 3.31 min, gradient 4-8 C3C/2 with.5 TFA over 6 min at a flow rate of.3 ml/min, C18 column. (Right) ESI- MS of 21. LRMS (ESI+) calcd. for C [(M+) + ]: 58.2, found: 58.4.

11 2 Fmoc 2 22 The product was purified by reversed- phase PLC (C18 column, gradient 26-56, C3C/2 with.5 TFA over 2 min). The fractions were collected and lyophilized to give 22 (12.22 mg, 14.4 µmol) as a white solid. C18, TW e+2 1: Range: 1.127e+2 C18, TW (2.48) Cm (348:354) e7 1.e+2 9.e+1 8.e+1 7.e+1 6.e+1 5.e+1 4.e+1 3.e+1 2.e e Figure S- 7. (Left) UV trace from UPLC- MS analysis of purified peptide 22; retention time = 2.35 min, gradient C3C/2 with.5 TFA over 6 min at a flow rate of.3 ml/min, C18 column. (Right) ESI- MS of 22. LRMS (ESI+) calcd. for C [(M+) + ]: 85.4, found: 85.4.

12 2 2 Fmoc 2 23 The product was purified by reversed- phase PLC (C18 column, gradient 27-57, C3C/2 with.5 TFA over 18 min). The fractions were collected and lyophilized to give 23 (14.37 mg, 13.6 µmol) as a white solid. C18, TW pure 1: Range: 1.265e+2 C18, TW pure 344 (2.359) Cm (34:346) e7 1.2e+2 1.1e+2 1.e+2 9.e+1 8.e+1 7.e+1 6.e+1 5.e e+1 3.e+1 2.e e Figure S- 8. (Left) UV trace from UPLC- MS analysis of purified peptide 23; retention time = 2.3 min, gradient C3C/2 with.5 TFA over 6 min at a flow rate of.3 ml/min, C18 column. (Right) ESI- MS of 23. LRMS (ESI+) calcd. for C [(M+) + ]: 158.5, found: 158.6, (M+2) 2+

13 S S 2 2 The product was purified by reversed- phase PLC (C18 column, gradient 13-24, C3C/2 with.5 TFA over 19 min). The fractions were collected and lyophilized to give 24 (23.32 mg, 21.5 µmol) as a white solid. 1 MR (6 Mz, DMS- d6, a mixture of carbamate rotamers) δ 9.21 (s, 1), 8.48 (d, J = 8.1 z, 1), 8.37 (d, J = 8. z, 1), 8.24 (dd, J = 21.7, 7.6 z, 2), 8.16 (d, J = 7.6 z, 1), (m, 5), (m, 2), (m, 7), (m, 3), 6.96 (d, J = 2.4 z, 1), 6.83 (d, J = 2.4 z, 1), (m, 2), (m, 2), (m, 1), (m, 3), 3.89 (p, J = 5.3 z, 1), (m, 3), 3.38 (d, J = 15.9 z, 1), 3.8 (ddt, J = 19.5, 14.2, 6.2 z, 3), 2.95 (ddd, J = 17.8, 11.4, 2.8 z, 2), (m, 5), (m, 2), (m, 3), (m, 4), (m, 3), 1.24 (d, J = 1.1 z, 1). 13 C MR (15 Mz, DMS- d6) δ , , , , 171.7, 17.97, 17.93, 17.67, 17.63, 17.62, , , , , , , , , , 13.2, 129.1, 128.2, 128., , , 118.5, 116.8, 116.7, 116.6, , , 59.73, 54.51, 53.76, 53.56, 53.2, 53.18, 52.31, 52.14, 49.48, 47.8, 41.78,

14 4.32, 37.24, 36.76, 36.41, 31.4, 29.12, 28.48, 28.17, 25.52, 25.38, 24.94, 24.4.; LRMS (ESI) calcd. for C S2 [(M+) + ]: 186.5; found: C18, TW-4-dvp 3.7 1:4 Range: 6.58 C18, TW-4-dvp 458 (3.118) Cm (454:473) e e Figure S- 9. (Left) UV trace from UPLC- MS analysis of purified dihydrovasopressin 24; retention time = 3.7 min, gradient C3C/2 with.5 TFA over 6 min at a flow rate of.3 ml/min, C18 column. (Right) ESI- MS of 24. LRMS (ESI+) calcd. for C S2 [(M+) + ]: 186.5; found: 186.6, (M+2) 2+

15 2 2 S 24 2 S S 24 2 S 2 2

16 S S 2 2 Vasopressin (25) To a solution of dihydrovasopressin 24 (1 mg, 9.26 µmol) in 2 (1 ml) was added a few drops of Ac. The p of the solution was adjusted to about 7 with 4. The solution was then aerated for about 6 h, at which time UPLC show the completion of the reaction. The crude vasopressin was obtained by lyophilization. The product was purified by reversed- phase PLC (C18 column, gradient 14-24, C3C/2 with.5 TFA over 18 min). The fractions were collected and lyophilized to give vasopressin 25 (7.1 mg, µmol) as a white solid. 1 MR (6 Mz, DMS-d6) δ 9.28 (s, 1), 8.7 (d, J = 8. z, 1), (m, 1), (m, 3), (m, 3), 7.96 (dt, J = 12.5, 6.5 z, 2), 7.57 (q, J = 6.6, 5.7 z, 1), (m, 1), (m, 7), (m, 1), 6.96 (dd, J = 24.4, 5.3 z, 3), (m, 3), (m, 2), 4.71 (p, J = 7.1 z, 1), (m, ), 4.52 (q, J = 6.8 z, 1), 4.4 (q, J = 8.3 z, 1), (m, 3), 4.2 (q, J = 9.6, 7.8 z, 1), 3.92 (dt, J = 1.2, 5.3 z, 1), (m, 4), (m, 1), (m, 4), 3.1 (td, J = 13.5, 6.7 z, 1), 2.92 (dd, J = 14., 1.1 z, 1), (m, 1), 2.59 (t, J = 8.3 z, 3), (m, 2), (m, 5), (m, 3), (m, 1).; 13 C MR

17 (15 Mz, DMS- d6, a mixture of carbamate rotamers) δ , , , , , 17.85, 17.73, 17.69, , , 158.1, 157.9, 157.7, 157.5, , , , 129.9, 129.9, , , , 115.2, 59.89, 55.75, 55.22, 53.95, 52.36, 51.83, 51.25, 49.75, 46.78, 41.84, 4.98, 4.66, 4.33, 36.62, 35.86, 31.35, 29.6, 28.3, 26.3, 24.99, 24.42, 1.14.; LRMS (ESI) calcd. for C S2 [(M+) + ]: 184.4; found: The identity of synthetic vasopressin and authentic vasopressin (American Peptide Company) was confirmed by co- injection in UPLC. C18, TW-4-AVP-co :43 Range: 6.29 C18, TW-4-syn-AVP 426 (2.92) Cm (42:431) e TW-4-Aut-AVP 2.8 Range: TW-4-syn-AVP 2.86 Range: Figure S- 1. (Left) UV trace from UPLC- MS analysis of purified vasopressin 25, authentic sample and co- injection; retention time = 2.83 min, gradient C3C/2 with.5 TFA over 6 min at a flow rate of.3 ml/min, C18 column. (Right) ESI- MS of 25. LRMS (ESI+) calcd. for C S2 [(M+) + ]: 184.4; found: 184.7, (M+2) 2+

18 2 2 S S Vasopressin Authentic Sample Vasopressin Synthetic Sample

19 2 2 S S Vasopressin Authentic Sample Vasopressin Synthetic Sample

20 Single amino acid derived thioacid was synthesized following the procedure documented in ref. 12, 19. Peptide- derived thioacid was synthesized following the procedure documented in ref. 11, S Fmoc 2 38 The product was purified by reversed- phase PLC (C18 column, gradient 31-61, C3C/2 with.5 TFA over 17 min). C18, 3-6 TW e+2 1: Range: 1.56e+2 C18, 3-6 TW (3.564) Cm (516:532) e7 1.e+2 9.5e+1 9.e+1 8.5e+1 8.e+1 7.5e+1 7.e+1 6.5e+1 6.e+1 5.5e+1 5.e+1 4.5e+1 4.e+1 3.5e+1 3.e+1 2.5e+1 2.e e+1 1.e Figure S- 11. (Left) UV trace from UPLC- MS analysis of purified 38; retention time = 3.49 min, gradient 3-6 C3C/2 with.5 TFA over 6 min at a flow rate of.3 ml/min, C18 column. (Right) ESI- MS of 38. LRMS (ESI+) calcd. for C344787S [(M+) + ]: 711.3, found:

21 Ac S 42 2 The product was purified by reversed- phase PLC (C18 column, gradient 5-25, C3C/2 with.5 TFA over 16 min). C18, 1-3 TW e :46 Range: 5.277e+1 C18, 1-3 TW (2.599) Cm (38:389) e7 4.75e+1 4.5e e+1 4.e e+1 3.5e e+1 3.e e+1 2.5e e+1 2.e e+1 1.5e e+1 1.e Figure S- 12. (Left) UV trace from UPLC- MS analysis of purified 42; retention time = 2.54 min, gradient 1-3 C3C/2 with.5 TFA over 6 min at a flow rate of.3 ml/min, C18 column. (Right) ESI- MS of 42. LRMS (ESI+) calcd. for C243787S [(M+) + ]: 581.3, found:

22 S Ac 2 45 The product was purified by reversed- phase PLC (C18 column, gradient 12-32, C3C/2 with.5 TFA over 18 min). C18, 13-33Ting Wang, sjd TW e :13:3614-ct-212 Range: 8.121e+1 C18, TW (19.36) Cm (1126:1171) e7 7.5e+1 7.e+1 6.5e+1 6.e+1 5.5e+1 5.e+1 4.5e+1 4.e+1 3.5e+1 3.e e+1 2.e+1 1.5e+1 1.e Figure S- 13. (Left) UV trace from PLC- MS analysis of purified 45; retention time = min, gradient C3C/2 with.5 TFA over 3 min at a flow rate of.3 ml/min, C18 column. (Right) ESI- MS of 45. LRMS (ESI+) calcd. for C34187S [(M+) + ]: 657.3, found:

23 2 2 2 Fmoc To the solid support peptide 37 (3.36 μmol) was added DMF (.3 ml), thioacid 38 (3.58 mg, 5.4 μmol), Bt (1.36 mg, 1.8 μmol) followed by t- BuC (1.14 μl, 1.8 μmol). The reaction mixture was shaken at ambient temperature 12 hours. The resin was then washed sequentially with C2Cl2/Me (1:1, v/v, 3 2 ml), DMF (3 2 ml) and Me (3 2 ml), dried by a stream of 2. To a suspension of the resulting solid support peptide 39 was added piperidine/dmf solution (1:4, v/v, 1 ml). The mixture was allowed to shake for 3 min before the solution was drained away. Another portion of piperidine/dmf solution (1:4, v/v, 1 ml) was added and the mixture was allowed to shake for 7 min. After drain away the DMF solution, the resin was then washed sequentially with C2Cl2/Me (1:1, v/v, 3 2 ml), DMF (3 2 ml) and Me (3 2 ml), dried by a stream of 2. To the resulting support peptide was added DMF (.3 ml), thioacid 38 (3.58 mg, 5.4 μmol), Bt (1.36 mg, 1.8 μmol) followed by t- BuC (1.14 μl, 1.8 μmol). The reaction mixture was shaken at ambient temperature 24 hours. The resin was then washed sequentially with C2Cl2/Me (1:1, v/v, 3 2 ml), DMF (3 2 ml) and Me (3 2 ml), dried by a stream of 2.

24 The resin cleavage of peptide product was executed by treatment of with TFA/TIPS/2 (1.5 ml/.1 ml/.1 ml) for 9 min. After removal of TFA by evaporation with a stream of 2, the residue was washed by cold ether, dissolved in C3C/2 (1:1, 5 ml) and lyophilized to yield crude peptide. The product was then purified by reversed- phase PLC (C18 column, gradient 28-53, C3C/2 with.5 TFA over 18 min). The fractions were collected and lyophilized to give 4 (4.28 mg, 2.62 µmol) as a white solid. C18, 3-55 TW pure 3.4e+1 1: Range: 3.446e+1 C18, 3-55 TW pure 443 (3.39) Cm (433:45) e7 3.2e+1 3.e+1 2.8e+1 2.6e+1 2.4e+1 2.2e+1 2.e+1 1.8e+1 1.6e+1 1.4e+1 1.2e+1 1.e Figure S- 14. (Left) UV trace from UPLC- MS analysis of purified 4; retention time = 2.97 min, gradient 3-55 C3C/2 with.5 TFA over 6 min at a flow rate of.3 ml/min, C18 column. (Right) ESI- MS of 4. LRMS (ESI+) calcd. for C S [(M+) + ]: , found: , , 189.6, 817.2, 545.4

25 Ac 2 43 To the solid support peptide 41 (3.73 μmol) was added DMF (.4 ml), thioacid 42 (4.32 mg, 7.46 μmol), Bt (2.52 mg, mmol) followed by t- BuC (2 μl, mmol). The reaction mixture was shaken at ambient temperature 15 hours. The resin was then washed sequentially with C2Cl2/Me (1:1, v/v, 3 2 ml), DMF (3 2 ml) and Me (3 2 ml), dried by a stream of 2. The resin cleavage of peptide product was executed by treatment of with TFA/TIPS/2 (3 ml/.15 ml/.15 ml) for 9 min. After removal of TFA by evaporation with a stream of 2, the residue was washed by cold ether, dissolved in C3C/2 (1:1, 5 ml) and lyophilized to yield crude peptide. The product was then purified by reversed- phase PLC (C18 column, gradient 5-25, C3C/2 with.5 TFA over 19 min). The fractions were collected and lyophilized to give 43 (1.93 mg, 3.1 µmol) as a white solid.

26 C18, 5-2 TW pure 1: Range: 4.162e+1 C18, 5-2 TW pure 517 (3.517) Cm (59:523) e6 3.8e+1 3.6e+1 3.4e+1 3.2e+1 3.e+1 2.8e+1 2.6e+1 2.4e+1 2.2e+1 2.e+1 1.8e+1 1.6e+1 1.4e+1 1.2e+1 1.e Figure S- 15. (Left) UV trace from UPLC- MS analysis of purified 43; retention time = 3.46 min, gradient 5-2 C3C/2 with.5 TFA over 6 min at a flow rate of.3 ml/min, C18 column. (Right) ESI- MS of 43. LRMS (ESI+) calcd. for C26499 [(M+) + ]: 622.3, found:

27 2 Ac To the solid support peptide 37 (3.73 μmol) was added DMF (.5 ml), thioacid 42 (4.32 mg, 7.46 μmol), Bt (2.52 mg, mmol) followed by t- BuC (2 μl, mmol). The reaction mixture was shaken at ambient temperature 2 hours. The resin was then washed sequentially with C2Cl2/Me (1:1, v/v, 3 2 ml), DMF (3 2 ml) and Me (3 2 ml), dried by a stream of 2. The resin cleavage of peptide product was executed by treatment of with TFA/TIPS/2 (3 ml/.15 ml/.15 ml) for 9 min. After removal of TFA by evaporation with a stream of 2, the residue was washed by cold ether, dissolved in C3C/2 (1:1, 5 ml) and lyophilized to yield crude peptide. The product was then purified by reversed- phase PLC (C18 column, gradient 8-28, C3C/2 with.5 TFA over 18 min). The fractions were collected and lyophilized to give 44 (3.2 mg, 3.6 µmol) as a white solid.

28 C18, 1-3 TW-4-82-pure 1: Range: 3.61e+1 C18, 1-3 TW-4-82-pure 471 (3.28) Cm (468:478) e7 3.4e+1 3.2e+1 3.e+1 2.8e+1 2.6e+1 2.4e+1 2.2e+1 2.e+1 1.8e+1 1.6e+1 1.4e+1 1.2e+1 1.e Figure S- 16. (Left) UV trace from UPLC- MS analysis of purified 44; retention time = 3.16 min, gradient 1-3 C3C/2 with.5 TFA over 6 min at a flow rate of.3 ml/min, C18 column. (Right) ESI- MS of 44. LRMS (ESI+) calcd. for C [(M+) + ]: 148.5, found: 148.7, (M+2) 2+

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