synthesis of amino acid derived glycoconjugates and ...456.1219electronic supplementary information...

Electronic Supplementary Information

Kiran Soni and Ajay K. Sah*

1

Synthesis of amino acid derived glycoconjugates and investigation

of their anti-inflammatory and analgesic properties

Kiran Soni, Ajay K. Sah*

Department of Chemistry, Birla Institute of Technology and Science, Pilani, Pilani

Campus, Rajasthan-333 031, India.

* To whom correspondence should be addressed. E-mail: [email protected], Fax: +91-1596-244183;

Tel: +91-1596-515662

Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013

mailto:[email protected]



2

1H NMR spectrum of Compound F2 recorded in DMSO-d6




3

13C NMR spectrum of Compound F2 recorded in DMSO-d6




4

1H NMR spectrum of Compound A2 recorded in DMSO-d6




5

13C NMR spectrum of Compound A2 recorded in DMSO-d6




6

1H NMR spectrum of Compound C2 recorded in DMSO-d6




7

13C NMR spectrum of Compound C2 recorded in DMSO-d6




8





9





10





11





12





13





14





15





16

1H-13C COSY NMR spectrum of compound C3 recorded in DMSO-d6




17

HRMS Spectra of C2

WATERS, Q-TOF MICROMASS (LC-MS) SAIF/CIL,PANJAB UNIVERSITY,CHANDIGARH

m/z75 100 125 150 175 200 225 250 275 300 325 350 375 400 425 450 475 500 525 550 575 600 625 650 675 700 725 750 775 800

%

0

100

KIRAN C-2+ 25 (0.380) AM (Top,4, Ar,5000.0,554.26,0.70,LS 10); Sm (Mn, 2x3.00); Sb (1,40.00 ); Cm (25:32) 1: TOF MS ES- 938174.9484

938

134.0263536

130.9635120

112.978294

272.0983824

265.145848188.9689

35

418.1616750

304.9055260

325.185849

339.194233

454.1396611

419.1570160

487.3080214

713.4880109

489.307587

497.313920 550.7966

5596.7583

4660.7802

3

715.490729 754.6870

1


m/z400 405 410 415 420 425 430 435 440 445 450 455 460 465 470 475 480 485 490

%

0

100

KIRAN C-2+ 25 (0.380) AM (Top,4, Ar,5000.0,554.26,0.70,LS 10); Sm (Mn, 2x3.00); Sb (1,40.00 ); Cm (25:32) 1: TOF MS ES- 750418.1616

750

412.82679

408.87267400.7975

5

454.1396611

419.1570160

420.183534 438.8444

29

434.889028424.8332

11451.3138

11446.1612

8

487.3080214456.1219

196

457.151142 471.1741

29458.1814;8

468.85385

485.18406

476.86186

489.307587




18

HRMS Spectra of C3


m/z75 100 125 150 175 200 225 250 275 300 325 350 375 400 425 450 475 500 525 550 575 600 625 650 675 700 725 750 775 800

%

0

100

KIRAN C-3 27 (0.399) AM (Top,4, Ar,5000.0,556.28,0.70,LS 10); Sm (Mn, 2x3.00); Sb (1,40.00 ); Cm (23:32) 1: TOF MS ES+ 2.42e4433.1453

24163

129.10207448

103.1247635

206.09534497

174.16262328 411.1766

1613237.16101085

277.1460315

357.1286280

299.1209275 393.1744

198

434.15734645

435.17071079 475.3262

587521.2739

296635.2449

279

567.209357

701.4962263

735.30042

786.25062


m/z404 406 408 410 412 414 416 418 420 422 424 426 428 430 432 434 436 438 440 442 444 446 448 450 452

%

0

100


24163

411.17661613

410.211323

405.274621

430.15611521

412.1825;348 422.1694237

416.178715

429.763149

427.308019

434.15734645

435.17071079 449.1312

953436.5101;174441.1530

77

447.145437

451.1421194




19

HRMS Spectra of C4


m/z75 100 125 150 175 200 225 250 275 300 325 350 375 400 425 450 475 500 525 550 575 600 625 650 675 700 725 750 775 800

%

0

100


23864

103.12402101

86.0992924

174.16148399

130.10811889

495.17224052

175.1634928 223.1511

565 473.1953449

268.1000407 303.2182

36455.1949

22419.1459

21375.1677

19

496.1786954

728.261086

628.350180

511.1330;57 583.292427

646.32593

753.302523


m/z465 470 475 480 485 490 495 500 505 510 515 520 525 530 535

%

0

100


4052

473.1953449

471.57912

492.1700192

474.2003102

484.180213

479.82651

491.3616;6

496.1786954

497.1751227

511.133057498.1727;34 505.5879

4

537.282555

518.234323

528.17322

526.18682

531.18242




20

HRMS Spectra of C5


m/z75 100 125 150 175 200 225 250 275 300 325 350 375 400 425 450 475 500 525 550 575 600 625 650 675 700 725 750 775 800

%

0

100


23095

103.12581881

174.16447367

130.11042033

518.19892988

303.22342045207.1174

1682258.1708

898

353.17531952

496.2196641

354.1899521 458.2254

223413.1445

169

519.2062867 753.3154

452701.5292107

538.2948;88632.7425

84

771.31124


m/z480 485 490 495 500 505 510 515 520 525 530 535 540 545 550 555

%

0

100


2988

496.2196641

495.202366

481.262554

491.230021

497.2270186 515.2047

171507.237289

505.214132

509.286419

519.2062867

537.3030250

520.2034227

534.1867194526.2293

168

523.2454;80 527.2333;58 538.294888

545.229866

550.200836

553.294731




21

HRMS Spectra of C6


m/z75 100 125 150 175 200 225 250 275 300 325 350 375 400 425 450 475 500 525 550 575 600 625 650 675 700 725 750 775 800

%

0

100


13117

129.10039121

102.12874352

86.09861148

258.15683834174.1602

3593237.1577

3186

192.10422426

282.11621396

509.18643467

304.22422436

487.2084997353.1668

651

481.2936302

366.2005;189

510.1849969

597.2816517511.2064;273 777.2570

144

749.2873130654.3286

113


m/z478 480 482 484 486 488 490 492 494 496 498 500 502 504 506 508 510 512 514 516 518 520 522 524

%

0

100


3467

487.2084997

481.2936302

479.206011

482.2965117

506.1857469488.2066

344

505.213097

489.216679 498.1910

73496.1968

11493.8718

6

500.200020

510.1849969

511.2064273

525.1580200

514.266155

523.232849

518.219620




22

ESI Figure 1. Anti-inflammatory chart for different drug molecules. *P < 0.01 with respect to control.




23

ESI Table 1. Analgesic activities of C1C6 on Swiss Albino mice using acetic acid induced writhing model

Label Dose(mg/kg, i.p.) No of writhingsa % Reduction in pain

symptoms

Acetic Acid

Control _ 9310.80 _

C1 100 50.63 94.62

C2 100 9.163.47 90.15

C3 100 116.25 88.17

C4 100 12.84.12 86.24

C5 100 7.161.66 92.30

C6 100 9.333.77 89.97

Aspirin 100 24.54.06 73.65

a indicates 0.01 > P with relative to Control


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