Supporting Information. Small molecule inhibitors that discriminate between protein arginine N- methyltransferases PRMT1 and CARM1
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1 Supporting Information Small molecule inhibitors that discriminate between protein arginine - methyltransferases PRMT1 and CARM1 James Dowden,* a Richard A. Pike, a Richard V. Parry, b Wei Hong, a Usama A. Muhsen, a and Stephen G. Ward b a School of Chemistry, University Park, University of ottingham, ottingham, G7 2RD, UK. Fax: +44 () ; Tel: +44 () ; james.dowden@nottingham.ac.uk b Department of Pharmacy and Pharmacology, University of Bath, Claverton Down, Bath, BA2 7AY, UK. Chemistry: Intermediates not explicitly described within the manuscript are detailed with characterisation in the same order below. These protected compounds are numbered P-o., where o. corresponds to the number of the denuded compound in the manuscript. General procedure for first reductive amination: method 1 5'-Amino-5'-deoxy-2',3'-,-(1-methylethylidene)adenosine 8 1 (1.2 mol eq.) and aldehyde 5, 2 6, or 12 5 (1. mol eq.) were suspended in ClCH 2 CH 2 Cl (5 ml) at room temperature under Ar and the mixture gently heated with vigorous stirring to obtain a solution. abh(ac) 3 (1.4 mol eq.) was slowly added portionwise and the reaction left for 2-4 hrs at room temperature under Ar. The reaction was then quenched by addition of saturated aqueous a 2 C 3 solution (5 ml). The mixture was extracted with CH 2 Cl 2 (3 x 5 ml) and the combined organic layers were dried over MgS 4 and concentrated in vacuo to yield the crude product. The product was purified by column chromatography on silica gel eluting with Me: CH 2 Cl 2, 5:95, unless specified otherwise. General procedure for second reductive amination: method 2 Secondary amines 9, 3 1 or 11 (1. mol eq.) and aldehydes 12, 5 13, 14, or 15 (1.1 mol eq.) with MgS 4 (1 mol eq.) were used, then as method 1 above. General procedure for deprotection: method 3 Intermediates from method 2 above were dissolved in TFA (4 ml) and water (.1 ml) and stirred overnight. The mixture was concentrated in vacuo, dissolved in water (5 ml) and washed with EtAc (2 x 5 ml). The aqueous layer was concentrated in vacuo to ~ 1mL then applied to a column of Amberlite IRA- 4 (Cl - ) ion exchange resin, eluted with water, and fractions containing product freeze dried to give the hydrochloride salts 16-18,
2 General procedure for Swern oxidations xalyl chloride (1.2 mol eq) was added into a solution of dry DMS (2.4 mol eq.) in dry CH 2 Cl 2 (15 ml) at -78 C and stirred for 3 mins under Ar. A solution of alcohol (1 mol eq.) in dry CH 2 Cl 2 (15 ml) was slowly added via cannula and the reaction stirred for 3 min. Dry Et 3 (5 mol eq.) was slowly added and the reaction stirred for 3 mins then slowly warmed to r.t. The reaction was quenched by the addition of H 2 (15 ml) and the mixture extracted with CH 2 Cl 2 (3 x 25 ml). The combined organic extracts were dried over MgS 4, filtered and concentrated. The product was purified by column chromatography on silica gel. 2,3-di(tert-Butoxycarbonyl)-1-(4-oxobutyl)guanidine (13) Swern oxidation of 2,3-di(tert-butoxycarbonyl)-1-(4-hydroxybutyl)-guanidine. 6 Elution with EtAc: petroleum ether (4/6) 2:8 gave the product as a clear oil (1.32 g, 88%), max / cm (w), 3285 (w), 37 (w), 2984 (w), 2935 (w), 1722 (s), 1636 (s), 1617 (s), 1417 (m), 1394 (w), 1369 (s), 1332 (s), 1289 (w), 1253 (w), 124 (w), 1158 (s), 1136 (s), 152 (w), 127 (w); 1 H MR H (4 MHz, CDCl 3 ) 9.8 (1H, s, CH), 8.37 (1H, br s, C()HCH 2 ), 3.45 (2H, app. q, J = 7.1, HCH 2 ), 2.54 (2H, t, J = 7., CH 2 CH), 1.92 (2H, quintet, J = 7.1, CH 2 CH 2 CH 2 ), 1.51 (18H, s, C(CH 3 ) 3 ); 13 C MR C (1 MHz, CDCl 3 ) 21.2 (CH), (C), (C), (C), 83.2 (C), 79.3 (C), 41.1 (CH 2 ), 4. (CH 2 ), 28.3 (CH 3 ), 28.2 (CH 3 ), 21.7 (CH 2 ); m/z (ESI) (1%, M + Me + H + ), 33.2 (24%, M + H + ) Found C 15 H requires ,3-di(tert-Butoxycarbonyl)-1-(5-oxopentyl)-guanidine (14) Swern oxidation of 2,3-di(tert-butoxycarbonyl)-1-(5-hydroxypentyl)-guanidine. 6 Elution with EtAc: petroleum ether (4/6) 3:7 gave the product as a white solid (.98 g, 81%), mp C; max / cm (w), 2986 (w), 2945 (w), 1722 (s), 1681 (m), 1635 (s), 1476 (w), 1455 (w), 1417 (s), 1394 (m), 1368 (s), 1334 (s), 128 (m), 1254 (m), 116 (s), 1136 (s), 154 (w), 989 (w); 1 H MR H (4 MHz, CDCl 3 ) 9.78 (1H, d, J = 1.4, CH), 8.34 (1H, br s, C()HCH 2 ), 3.45 (2H, app. q, J = 7., HCH 2 ), 2.5 (2H, td, J = 7.2, 1.4, CH 2 CH), (4H, m, CH 2 CH 2 CH 2 CH 2 ), 1.51 (9H, s, C(CH 3 ) 3 ), 1.5 (9H, s, C(CH 3 ) 3 ); 13 C MR C (1 MHz, CDCl 3 ) 22. (CH), (C), (C), (C), 83.1 (C), 79.3 (C), 43.4 (CH 2 ), 4.4 (CH 2 ), 28.5 (CH 2 ), 28.3 (CH 3 ), 28.1 (CH 3 ), 19.3 (CH 2 ); m/z (ESI) (39%, M + Me + H + ), (1%, M + H + ) Found C 16 H requires
3 1-[4-(formyl)phenyl]-2,3-bis-(tert-butoxycarbonyl)guanidine (15) Swern oxidation of 1-[4-(hydroxymethyl)phenyl]([2,3-bis-(tertbutoxycarbonyl)guanidine. 7 Elution with EtAc: petroleum ether (4/6) 1:9 gave the product as a white solid (1.545 g, 5%), mp 133 C (dec.) (CH 2 Cl 2 ); max / cm (w), 2986 (w), 2936 (w), 283 (w), 2744 (w), 1722 (m), 1698 (m), 1637 (s), 159 (s), 1558 (s), 1476 (w), 1455 (w), 1413 (s), 137 (m), 1342 (m), 137 (s); 1 H MR H (4 MHz, CDCl 3 ) (1H, br s, H), 1.67 (1H, s, H), 9.94 (1H, s, CH), (4H, m, ArH), 1.55 (18H, s, C(CH 3 ) 3 ); 13 C MR C (1 MHz, CDCl 3 ) 191. (C), (C), (Cx2), (C), 13.9 (CH), (CH), 84.3 (C), 8.2 (C), 28.1 (CH 3 ); m/z (ESI) (1%, 2M + a + ), (39%, M + a + ), (38%, M + H + ) Found C 18 H requires '-[[(3S)-4-(tert-butoxy)-3-[[(tert-butoxy)carbonyl]amino]-4-oxobutyl]amino]- 5'-deoxy-2',3'--(1-methylethylidene)-adenosine (9) 2 2 Method 1. Column chromatography on silica gel, elution with EtAc:Me, 25:1, gave secondary amine 9 as a white solid (.9 g, 73%), mp C; [ ] 23 D (c 1.7 in CHCl 3 ); max / cm (w), 3414 (w), 298 (m), 2933 (m), 177 (s), 1632 (s), 1589 (s), 1328 (s), 1151 (s), 177 (m); 1 H MR H (4 MHz; CDCl 3 ) 8.33 (1H, s, ArH), 7.93 (1H, s, ArH), 6.6 (2H, s, adenosine-h 2 ), 6. (1H, d, J = 8.4, HBoc), 5.98 (1H, d, J = 3.6, 1'-H), 5.5 (1H, dd, J = 6.2, 3.6, 2'-H), 5.8 (1H, dd, J = 6.2, 3.2, 3'-H), (1H, m, 4'-H), (1H, m, CHCH 2 CH 2 ), 2.96 (1H, dd, J = 12.7, 3.8, 5'-CH a H b ), 2.8 (1H, dd, J = 12.7, 5.2, 5'-CH a H b ), (1H, m, CH a H b H), (1H, m, CH a H b H), (2H, m, CHCH 2 CH 2 ) 1.62 (3H, s, CH 3 ), 1.51 (9H, s, C(CH 3 ) 3 ), 1.4 (3H, s, CH 3 ), 1.38 (s, 9H, C(CH 3 ) 3 ); 13 C MR C (1 MHz; CDCl 3 ) (C), (C), (C), (CH), (C), (CH), 12.4 (C), (C), 91.1 (CH), 85. (CH), 83. (CH), 82.2 (CH), 81.7 (C), 79.4 (C), 53. (CH), 51.4 (CH 2 ), 46.3 (CH 2 ), 32.3 (CH 2 ), 28.3 (CH 3 ), 28. (CH 3 ), 27.4 (CH 3 ), 25.5 (CH 3 ); m/z (ESI) (1%, M + H + ) Found C 26 H requires
4 5'-[3-[2,3-di-(tert-butoxycarbonyl)guanidino]propyl]amino]-5'-deoxy-2',3'-- (1-methylethylidene)-adenosine Method 1. Elution Me: CH 2 Cl 2, from 1:9 to 15:85 gave the product as a white solid (.516 g, 43%), mp C (CH 2 Cl 2 ); [ ] 19 D (c 1. in CHCl 3 ); max / cm (m), 2936 (w), 1721 (m), 1632 (s), 1588 (s), 1473 (w), 1456 (w), 1417 (m), 1393 (w), 1369 (s), 133 (s); 1 H MR H (4 MHz; CDCl 3 ) 8.46 (1H, br s, H), 8.32 (1H, s, ArH), 7.95 (1H, s, ArH), 6.1 (1H, d, J = 3.1, 1'- H), 5.98 (2H, br s, adenosine-h 2 ), 5.47 (1H, dd, J = 6.4, 3.1, 2'-H), 5.2 (1H, dd, J = 6.4, 3.3, 3'-H), (1H, m, 4'-H), (2H, m, C()HCH 2 ), (2H, m, 5'-CH 2 ), (2H, m, CH 2 H), 1.7 (2H, quin, J = 6.8, CH 2 CH 2 H), 1.6 (3H, s, CH 3 ), 1.48 (18H, s, C(CH 3 ) 3 ), 1.38 (3H, s, CH 3 ); 13 C MR C (1 MHz; CDCl 3 ) (C), (C), (C), (C), (CH), (C), (CH), 12.3 (C), (C), 9.8 (CH), 58.6 (CH), 83.5 (CH), 82.9 (C), 82.4 (CH), 79.2 (C), 51.3 (CH 2 ), 47.1 (CH 2 ), 38.9 (CH 2 ), 29.1 (CH 2 ), 28.2 (CH 3 ), 28. (CH 3 ), 27.2 (CH 3 ), 25.4 (CH 3 ); m/z (ESI) 66.3 (M + H +,1%) Found C 27 H requires ; Calc. for C 27 H
5 5'-deoxy-5'-[[(3S)-4-(tert-butoxy)-3-[[(1,1 dimethylethoxy)carbonyl]amino]-4- oxobutyl] [(3-(tert-butoxycarbonyl)aminopropyl]amino]-2',3'--(1- methylethylidene)-adenosine (P19) t 2 2 Method 2. gave a white solid (.447 g, 71%), mp C (CH 2 Cl 2 ); [ ] 23 D (c 1.5 in CHCl 3 ); max / cm (w), 2984 (m), 2936 (w), 1712 (s), 1633 (s), 164 (w), 155 (m), 1369 (s), 1248 (m), 1158 (s); 1 H MR H (4 MHz; CDCl 3 ) 8.33 (1H, s, ArH), 7.93 (1H, s, ArH), 6.7 (1H, d, J = 1.5, 1'-H), 5.87 (2H, br s, H 2 ), (2H, m, 2'-H and H), (1H, br m, 3'-H), (1H, m, 4'-H), (1H, br m, CHCH 2 ), (2H, m, HCH 2 ), 2.74 (1H, dd, J = 13., 7.5, 5'-CH a H b ), (1H, m, CHCH 2 CH a H b ), (2H, m, 5'- CH a H b and HCH 2 CH 2 CH a H b ), (2H, m, CHCH 2 CH a H b and HCH 2 CH 2 CH a H b ), (1H, br m, CHCH a H b ), (1H, m, CHCH a H b ), 1.63 (3H, s, CH 3 ), (2H, m, HCH 2 CH 2 CH 2 ), 1.45 (9H, s, C(CH 3 ) 3 ), 1.44 (18H, s, C(CH 3 ) 3 ), 1.41 (3H, s, CH 3 ); 13 C MR C (1 MHz; CDCl 3 ) (C), (C), (C), 153. (CH), (C), 14.2 (CH), 12.3 (C), (C), 9.9 (CH), 85.7 (CH), 84. (CH), 83.5 (CH), 81.7 (C), 79.6 (C), 78.8 (C), 77.2 (C), 56.1 (CH 2 ), 52.8 (CH), 51.6 (CH 2 ), 5.5 (CH 2 ), 38.2 (CH 2 ), 29.3 (CH 2 ), 28.5 (CH 3 ), 28.4 (CH 3 ), 28. (CH 3 ), 27.1 (CH 3 ), 26.9 (CH 2 ), 25.5 (CH 3 ); m/z (ESI) (1%, M + H + ) Found C 34 H requires ;
6 5'-deoxy-5'-[[(3S)-4-(tert-butoxy)-3-[[(1,1 dimethylethoxy)carbonyl]amino]-4- oxobutyl][[4-[2,3-bis-(tert-butoxycarbonyl)]guanidinophenyl]methyl]amino]- 2',3'--(1-methylethylidene)-adenosine (P2) Method 2 gave the product as a white solid (.57 g, 71%), mp C (CH 2 Cl 2 ); [ ] 26 D -1.3 (c 1. in CHCl 3 ); max / cm (s), 2985 (m), 2937 (m), 1714 (s), 1633 (s), 166 (s), 1564 (m), 156 (m), 1476 (m), 1456 (m), 1416 (s), 1394 (s), 137 (m), 134 (s), 133 (m), 124 (s), 1154 (s); 1 H MR H (4 MHz; CDCl 3 ) (1H, s, H), 1.26 (1H, s, H), 8.24 (1H, s, ArH), 7.8 (1H, s, ArH), 7.46 (2H, d, J = 7.8, ArH), 7.16 (2H, d, J = 7.8, ArH), 6.5 (1H, br m, 1'-H), 5.69 (2H, s, adenosine-h 2 ), 5.62 (1H, br m, H), 5.37 (1H, d, J = 5.4, 2'-H), (1H, br m, 3'-H), (1H, br m, 4'-H), (1H, br m, CHCH 2 ), 3.62 (1H, d, J = 13.4, ArCH a H b ), 3.43 (1H, d, J = 13.4, ArCH a H b ), (4H, m, 5'-CH 2 and CHCH 2 CH 2 ), (1H, m, CHCH a H b ), (1H, m, CHCH a H b ), 1.61 (3H, s, CH 3 ), 1.55 (9H, s, (CH 3 ) 3 ), 1.49 (9H, s, (CH 3 ) 3 ), 1.45 (9H, s, C(CH 3 ) 3 ), 1.43 (9H, s, C(CH 3 ) 3 ), 1.38 (3H, s, CH 3 ); 13 C MR C (1 MHz; CDCl 3 ) (C), (C), (C), (C x 2), (C), (CH), (C), (CH), (C), (C), (CH), (CH), 12.3 (C), (C), 9.7 (CH), 85.3 (CH), 83.8 (CH), 83.7 (C), 83.4 (CH), 81.6 (C), 79.6 (C), 79.4 (C), 58.3 (CH 2 ), 55.5 (CH 2 ), 53. (CH), 5.7 (CH 2 ), 29.3 (CH 2 ), 28.4 (CH 3 ), 28.2 (CH 3 ), 28.1 (CH 3 ), 28. (CH 3 ), 27.1 (CH 3 ), 25.4 (CH 3 ); m/z (ESI) (1%, M + H + ) Found C 44 H requires ;
7 5'-deoxy-5'-[[(4-(tert-butoxy)-4-oxobutyl][3-[2,3-di-(tert- butoxycarbonyl)guanidino]propyl]amino]-2',3'--(1-methylethylidene)- adenosine (P21) Method 2. White solid (.468 g, 79%), mp C (CH 2 Cl 2 ); [ ] 26 D (c 1. in CHCl 3 ); max / cm (m), 172 (s), 1633 (s), 1588 (s), 1475 (m), 1456 (w), 1418 (m), 1369 (s), 1331 (s), 129 (m), 124 (m), 1157 (s), 1135 (s); 1 H MR H (4 MHz; CDCl 3 ) 11.5 (1H, s, H), 8.44 (1H, br m, H), 8.36 (1H, s, ArH), 7.97 (1H, s, ArH), 6.5 (1H, d, J = 2.1, 1'-H), 5.73 (2H, s, adenosine-h 2 ), 5.52 (1H, dd, J = 6.4, 2.1, 2'-H), 4.97 (1H, dd, J = 6.4, 3.2, 3'-H), 4.34 (1H, app. td, J = 6.8, 3.2, 4'-H), (2H, m, HCH 2 ), 2.74 (1H, dd, J = 13.6, 6.8, 5'-CH a H b ), 2.58 (1H, dd, J = 13.6, 6.8, 5'-CH a H b ), (4H, m, CCH 2 CH 2 CH 2 and HCH 2 CH 2 CH 2 ), (2H, m, CCH 2 CH 2 CH 2 ), (4H, m, CCH 2 CH 2 CH 2 and HCH 2 CH 2 CH 2 ), 1.6 (3H, s, CH 3 ), 1.5 (18H, s, C(CH 3 ) 3 ), 1.43 (9H, s, C(CH 3 ) 3 ), 1.39 (3H, s, CH 3 ); 13 C MR C (1 MHz; CDCl 3 ) (C), (C), (C), (C), (C), (CH), (C), 14.2 (CH), 12.3 (C), (C), 91. (CH), 85.6 (CH), 83.7 (CH), 83.4 (CH), 82.9 (C), 8.1 (C), 79.2 (C), 56.1 (CH 2 ), 53.5 (CH 2 ), 52. (CH 2 ), 39.3 (CH 2 ), 33.1 (CH 2 ), 28.3 (CH 3 ), 28.1 (CH 3 ), 28.8 (CH 3 ), 27.1 (CH 3 ), 26.5 (CH 2 ), 25.3 (CH 3 ), 22. (CH 2 ); m/z (ESI) (1%, M + H + ) Found C 35 H requires ; Calc. for C 35 H
8 5'-[3-[2,3-di-(tert-butoxycarbonyl)guanidino]propyl][(3-(tert- butoxycarbonyl)aminopropyl]amino]-5'-deoxy-2',3'--(1-methylethylidene)- adenosine (P22) 2 Method 2. Column chromatography on silica gel (Me:CH 2 Cl 2 5:95 to 1:9) gave the product as a white solid (.187 g, 35%), mp C (CH 2 Cl 2 ); [ ] 23 D (c 1.5 in CHCl 3 ); max / cm (w), 3328 (w), 2984 (m), 1712 (s), 1632 (s), 156 (w), 1473 (w), 1417 (m), 1393 (w), 1368 (s), 133 (m), 1289 (m), 1248 (m), 1158 (s), 1136 (s); 1 H MR H (4 MHz; CDCl 3 ) (1H, br s, H), 8.35 (1H, br s, H), 8.31 (1H, s, ArH), 7.95 (1H, s, ArH), 6.9 (2H, br s, H 2 ), 6.5 (1H, d, J = 1.9, 1'-H), 5.92 (1H, br m, 2'-H), 5.55 (1H, br m, H), 5.5 (1H, dd, 6.4, 3.2, 3'-H), 4.82 (1H, m, 4'-H), 3.41 (2H, td, J = 6.9, 5.4, CCH 2 ), (2H, m, C()HCH 2 ), 2.65 (1H, dd, J = 13.3, 7., 5'-CH a H b ), (2H, m, 5'-CH a H b and CCH 2 CH 2 CH 2 ), (2H, m, C()HCH 2 CH 2 CH 2 ), 1.59 (3H, s, CH 3 ), 1.47 (18H, s, C(CH 3 ) 3 x 2), (4H, m, CCH 2 CH 2 CH 2 and C()HCH 2 CH 2 CH 2 ), 1.41 (9H, s, C(CH 3 ) 3 ), 1.38 (3H, s, CH 3 ); 13 C MR C (1 MHz; CDCl 3 ) (C), 156. (C), (C), (C), 153. (CH), (C), 14.1 (CH), 12.2 (C), (C), 9.8 (CH), 85.7 (CH), 83.8 (CH), 83.4 (CH), 82.9 (C), 79.1 (C x 2), 78.7 (C), 56.1 (CH 2 ), 53.4 (CH 2 ), 51.5 (CH 2 ), 39. (CH 2 ), 38.5 (CH 2 ), 28.4 (CH 3 ), 28.2 (CH 3 ), 28. (CH 3 ), 27. (CH 3 ), 26.5 (CH 2 ), 26.2 (CH 2 ), 25.3 (CH 3 ); m/z (ESI) 763 (1%, M + H + ) Found C 35 H requires
9 5'-[di(3-(tert-butoxycarbonyl)aminopropyl]amino]-5'-deoxy-2',3'--(1- methylethylidene)-adenosine (P23) Method 2. White solid (.421 g, 75%), mp C (CH 2 Cl 2 ); [ ] 21 D (c 1. in CH 2 Cl 2 ); max / cm (m), 2982 (s), 2819 (w), 176 (s), 1631 (s), 1588 (m), 158 (s), 1473 (m), 1423 (w), 1392 (w), 1368 (s), 133 (w), 1248 (m), 1167 (s); 1 H MR H (4 MHz; CDCl 3 ) 8.32 (1H, s, ArH), 7.94 (1H, s, ArH), 6.8 (1H, d, J = 1.6, 1'-H), 6.2 (2H, s, adenosine-h 2 ), (1H, m, 2'-H), (2H, s, H), (1H, m, 3'-H), (1H, m, 4'-H), (4H, m, HCH 2 CH 2 CH 2 ), (1H, m, 5'-CH a H b ), (1H, m, 5'-CH a H b ), (4H, m, HCH 2 CH 2 CH 2 ), 1.62 (3H, s, CH 3 ), (4H, m, HCH 2 CH 2 CH 2 ), 1.43 (18H, s, C(CH 3 ) 3 ), 1.41 (3H, s, CH 3 ); 13 C MR C (1 MHz; CDCl 3 ) (C), (C), 153. (CH), (C), 14.3 (CH), 12.3 (C), (C), 9.9 (CH), 85.9 (CH), 84. (CH), 83.4 (CH), 78.9 (C), 56.2 (CH 2 ), 51.6 (CH 2 ), 38.6 (CH 2 ), 28.7 (CH 3 ), 28.5 (CH 3 ), 27. (CH 3 ), 26.8 (CH 2 ), 25.4 (CH 3 ); m/z (ESI) (1%, M + H + ) Found C 29 H requires
10 5'-5'-deoxy-[di[2,3-di-(tert-butoxycarbonyl)guanidino]propyl]amino]-2',3'-- (1-methylethylidene)-adenosine (P24) 2 Method 2. Elution with Me:CH 2 Cl 2 5:95 to 1:9 gave the product as a white solid (.181 g, 3%), mp C (CH 2 Cl 2 ); [ ] 21 D (c 1. in CH 2 Cl 2 ); max / cm (w), 2985 (m), 2938 (m), 1721 (s), 1632 (s), 1587 (s), 1474 (m), 1455 (m), 1417 (s), 1394 (m), 1369 (s), 133 (s), 1157 (s), 1135 (s),; 1 H MR H (4 MHz; CDCl 3 ) (2H, s, (C()HC) 2 ), 8.42 (2H, br m, (C()HCH 2 ) 2 ), 8.34 (1H, s, ArH), 7.99 (1H, s, ArH), 6.5 (1H, d, J = 2.1, 1'-H), 5.76 (2H, br s, adenosine-h 2 ), 5.54 (1H, dd, J = 6.4, 2.1, 2'-H), 4.97 (1H, dd, J = 6.4, 3.3, 3'-H), 4.34 (1H, app. td, J = 6.7, 3.3, 4'-H), (4H, m, (HCH 2 CH 2 CH 2 ) 2 ), 2.72 (1H, dd, J = 13.6, 6.7, 5'-CH a H b ), (5H, m, 5'-CH a H b and (HCH 2 CH 2 CH 2 ) 2 ), (4H, m, (HCH 2 CH 2 CH 2 ) 2 ), 1.59 (3H, s, CH 3 ), 1.49 (36H, s, C(CH 3 ) 3 x 4), 1.38 (3H, s, CH 3 ); 13 C MR C (1 MHz; CDCl 3 ) (C x 2), (C), (C), (CH), (C), 14.3 (CH), 12.3 (C), (C), 9.9 (CH), 85.5 (CH), 83.6 (CH), 83.4 (CH), 82.9 (C), 79.1 (C), 56. (CH 2 ), 52. (CH 2 ), 39.3 (CH 2 ), 28.3 (CH 3 ), 28. (CH 3 ), 27. (CH 3 ), 26. (CH 2 ), 25.2 (CH 3 ); m/z (ESI) 95.5 (M + H +,1%), Found C 41 H requires ; References 1. A. M. Reeve, C. A. Townsend, Tetrahedron 1998, 54, R. M. Werner,.Shokek and J. T. Davis, J. rg. Chem. 1997, 62, M. Kolb, J. Barth, J.-G. Heydt and M. J. Jung, J. Med. Chem. 1987, 3, S. Hourcade, A. Ferdenzi, P. Retailleau, S. Mons and C. Marazano, Eur. J. rg. Chem., 25, S. Freeman,Y. Tal-Gan, S. Klein, A. Levitzki and C. Gilon, J. rg. Chem. 211, 76, eubert B. J.; Snider B. B. rg. Lett. 23, 5, Thuring J. W.; Li H.; Porter. A. Biochemistry 22, 41,
11 H 2 H 2 H H H H
12 H 2 H 2 H H H H
13 @7 Celcius H 2 H 2 H H H H
14 This Print journal Date: is 25 The Feb Royal 21 Society 15:46:52 of Chemistry 211 MS Data Review All Plots - 2/25/21 3:46 PM File: c:\varianws\data\dmt\18129\rp116,8 _ pm.xms Sample: RP116,8 Scan Range: Time Range: min. kcounts 2.:6.> 1 perator: dmt Date: 12/18/29 2:5 PM RP116,8 _ PM.xms TIC uv 3 2.:6.> 1A RP116,8 _ PM.xms uv % Spectrum 1A BP: 467 (3136=1%), rp116,8 _ pm.xms minutes min, Scans: 98-1, 2.:6.>, Ion: 1 us, RIC: % 5% 25% % m/z
15 H 2 H 2 H H H 2 H M1(d)
16 H 2 H 2 H H H H
17 @7 Celcius H 2 H 2 H H H H
18 This Print journal Date: is 25 The Feb Royal 21 Society 16:45:54 of Chemistry 211 MS Data Review All Plots - 2/25/21 4:45 PM File: c:\varianws\data\dmt\22129\rp124,8 _ am.xms Sample: RP124,8 Scan Range: Time Range: min. kcounts 1 2.:6.> perator: dmt Date: 12/22/29 9:5 AM RP124,8 _ AM.xms TIC uv 3 2.:6.> 1A RP124,8 _ AM.xms uv % Spectrum 1A BP: 481 (384=1%), rp124,8 _ am.xms minutes min, Scans: 92-94, 2.:6.>, Ion: 1 us, RIC: % 5% 25% % m/z
19 H 2 H 2 H H H H M1(d)
20 H 2 H 2 H H H H
21 @7 Celcius H 2 H 2 H H H H
22 This Print journal Date: is 25 The Feb Royal 21 Society 16:52:11 of Chemistry 211 MS Data Review All Plots - 2/25/21 4:52 PM File: c:\varianws\data\dmt\22129\rp125,8 _ am.xms Sample: RP125,8 Scan Range: Time Range: min. kcounts 1 2.:6.> perator: dmt Date: 12/22/29 9:5 AM RP125,8 _ AM.xms TIC uv 3 2.:6.> 1A RP125,8 _ AM.xms uv % Spectrum 1A BP: 495 (14617=1%), rp125,8 _ am.xms minutes min, Scans: 95-97, 2.:6.>, Ion: 1 us, RIC: % % 25% % m/z
23 H 2 H 2 H H M1(d)
24 H H H 2 H
25 @7 Celcius H 2 H 2 H H
26 This Print journal Date: is 25 The Feb Royal 21 Society 16:55:29 of Chemistry 211 MS Data Review All Plots - 2/25/21 4:55 PM File: c:\varianws\data\dmt\2911\rp135d,1v _ am.xms Sample: RP135d,1v Scan Range: Time Range: min. kcounts :65.> perator: dmt Date: 1/29/21 11:26 AM RP135d,1v _ AM.xms TIC nv 2.:65.> 1A RP135d,1v _ AM.xms uv % Spectrum 1A BP: 29 (2294=1%), rp135d,1v _ am.xms minutes 8.25 min, Scans: , 2.:65.>, Ion: us, RIC: % % 25% % m/z
27 H 2 H 2 H H + H 2 H M3(d) M4(d) M2(d) M1(dd)
28 H 2 H 2 H H + H 2 H
29 @ 7 Celcius H 2 H 2 H H + H 2 H
30 This Print journal Date: is 25 The Feb Royal 21 Society 17:25:23 of Chemistry 211 MS Data Review All Plots - 2/25/21 5:25 PM File: c:\varianws\data\dmt\121\rp183d,1v _ pm.xms Sample: RP183d,1v Scan Range: Time Range: min. kcounts 2.:65.> 15. perator: dmt Date: 2/1/21 3:35 PM RP183d,1v _ PM.xms TIC nv 3 2.:65.> 1A RP183d,1v _ PM.xms uv % Spectrum 1A BP: 215 (62=1%), rp183d,1v _ pm.xms minutes min, Scans: , 2.:65.>, Ion: us, RIC: % % 25% % m/z
31 H 2 H H H H M1(d)
32 H 2 H H H H
33 @7 Celcius H 2 H H H H
34 This Print journal Date: is 25 The Feb Royal 21 Society 16:57:11 of Chemistry 211 MS Data Review All Plots - 2/25/21 4:57 PM File: c:\varianws\data\dmt\121\rp181d,1v _ pm.xms Sample: RP181d,1v Scan Range: Time Range: min. kcounts 3 2.:65.> perator: dmt Date: 2/1/21 2:2 PM RP181d,1v _ PM.xms TIC nv 6 2.:65.> 1A RP181d,1v _ PM.xms uv % Spectrum 1A BP: 452 (1779=1%), rp181d,1v _ pm.xms minutes min, Scans: , 2.:65.>, Ion: 1 us, RIC: % 5% 25% % m/z
35 H 2 H 2 H H H H
36 @7 Celcius H 2 H 2 H H H H
37 H 2 H 2 H H H H
38 H 2 H 2 H H H H
39 This Print journal Date: is 25 The Feb Royal 21 Society 17:5:44 of Chemistry 211 MS Data Review All Plots - 2/25/21 5:5 PM File: c:\varianws\data\dmt\121\rp279,1v _ am.xms Sample: RP279,1v Scan Range: 1-9 Time Range: min. kcounts 2.:65.> 3 perator: dmt Date: 2/1/21 11:7 AM RP279,1v _ AM.xms TIC uv :65.> 1A RP279,1v _ AM.xms uv % Spectrum 1A BP: 423 (458=1%), rp279,1v _ am.xms minutes min, Scans: , 2.:65.>, Ion: us, RIC: % 5% 25% % m/z
40 This Print journal Date: is 25 The Feb Royal 21 Society 17:6:15 of Chemistry 211 MS Data Review All Plots - 2/25/21 5:6 PM File: c:\varianws\data\dmt\121\rp279,1v _ am.xms Sample: RP279,1v Scan Range: 1-9 Time Range: min. kcounts 2.:65.> 3 perator: dmt Date: 2/1/21 11:7 AM RP279,1v _ AM.xms TIC uv :65.> 1A RP279,1v _ AM.xms uv % Spectrum 1A BP: 233 (1536=1%), rp279,1v _ am.xms minutes 3.4 min, Scans: 88-9, 2.:65.>, Ion: 1 us, RIC: % % % % m/z
41 H 2 H 2 H H M2(t) M1(d)
42 H 2 H 2 H H
43 @7 Celcius H 2 H 2 H H
44 This Print journal Date: is 25 The Feb Royal 21 Society 17:17:3 of Chemistry 211 MS Data Review All Plots - 2/25/21 5:17 PM File: c:\varianws\data\dmt\121\rp278,1v _ pm.xms Sample: RP278,1v Scan Range: Time Range: min. kcounts 35 2.:65.> perator: dmt Date: 2/1/21 12:9 PM RP278,1v _ PM.xms TIC uv :65.> RP278,1v _ PM.xms uv A % Spectrum 1A BP: 246 (249=1%), rp278,1v _ pm.xms minutes min, Scans: , 2.:65.>, Ion: us, RIC: % % 25% % m/z
45 This Print journal Date: is 25 The Feb Royal 21 Society 17:17:59 of Chemistry 211 MS Data Review All Plots - 2/25/21 5:17 PM File: c:\varianws\data\dmt\121\rp278,1v _ pm.xms Sample: RP278,1v Scan Range: Time Range: min. kcounts 35 2.:65.> perator: dmt Date: 2/1/21 12:9 PM RP278,1v _ PM.xms TIC uv :65.> 1A RP278,1v _ PM.xms uv % Spectrum 1A BP: 423 (2939=1%), rp278,1v _ pm.xms minutes 3.57 min, Scans: 89-91, 2.:65.>, Ion: 1 us, RIC: % 5% 25% % m/z
46 H H 2 H H 2 H H H H M1(d) M2(dd)
47 H H 2 H H 2 H H H H
48 @7 Celcius H H 2 H H 2 H H H H
49 This Print journal Date: is 25 The Feb Royal 21 Society 17:9:16 of Chemistry 211 MS Data Review All Plots - 2/25/21 5:9 PM File: c:\varianws\data\dmt\2911\rp28,1v _ pm.xms Sample: RP28,1v Scan Range: Time Range: min. kcounts 2.:65.> 5 perator: dmt Date: 1/29/21 2:46 PM RP28,1v _ PM.xms TIC uv 3 2.:65.> 1A RP28,1v _ PM.xms uv % Spectrum 1A BP: 465 (11972=1%), rp28,1v _ pm.xms minutes 3.16 min, Scans: 91-93, 2.:65.>, Ion: 1 us, RIC: % 5% % % m/z
50 Information added after peer-review: Table 1: Distances (Å) measured between nearest oxygen of binding site residue and nearest nitrogen of guanidinium for flexibly docked ligand and rigid CARM1 receptor, or overlaid PRMT1 (bold) Residue E E Asn Glu Residue + H 3 E E Asn Glu Figure 1: Docked structure of 18 showing numbering of nitrogens in Table 1 above
51 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry Further images relevant to the Docking discussion: Figure 2: Result of docking inhibitor 2 (white backbone) with CARM1 binding site (2Y1X.pdb, selected residues green backbone), also AdoHcy 2 (yellow), substrate arginine channel (green mesh). PRMT1 residue superimposed, Glu47 (orange, bold in parentheses). Figure 3: Result of docking inhibitor 19 (white backbone) with CARM1 binding site (2Y1X.pdb, selected residues green backbone), also AdoHcy 2 (yellow), substrate arginine channel (green mesh). PRMT1 residue superimposed, Glu47 (orange, bold in parentheses).
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