Glycocluster synthesis by native chemical ligation

Synthesis

Volumn , Issue 18, 2010, Pages 3070-3082

  Wehner, Johannes W ^a   Lindhorst, Thisbe K ^a  

^a UNIVERSITY OF KIEL   (Germany)

Author keywords

carbohydrates; glycoclusters; glycopeptides; native chemical ligation; protecting group free synthesis

Indexed keywords

DERIVATIZATIONS; GLYCOCLUSTERS; GLYCOPEPTIDES; NATIVE CHEMICAL LIGATION; PROTECTING-GROUP-FREE SYNTHESIS; THIOESTERS;

AMINO ACIDS; CARBOHYDRATES; PEPTIDES; PHOSPHATASES;

SYNTHESIS (CHEMICAL);

(TRIPHENYLMETHYL)CYSTEINE [2 (2,3,4,6 TETRA O ACETYL ALPHA MANNOPYRANOSYLOXY)ETHYL]AMIDE; 2 [4 (ALPHA MANNOPYRANOSYLOXY)PHENYL]THIOACETIC ACID S PHENYL ESTER; 4 (CARBOXYLMETHYL)PHENYL ALPHA MANNOPYRANOSIDE; 4 (METHOXYCARBONYLMETHYL)PHENYL 2,3,4,6 TETRA O ACETYL ALPHA MANNOPYRANOSIDE; 4 (METHOXYCARBONYLMETHYL)PHENYL ALPHA MANNOPYRANOSIDE; [3 (ALPHA MANNOPYRANOSYLOXY)PROPYL]CYSTEINE ETHYL ESTER; CYSTEINE 2 [2 (2,3,4,6 TETRA O ACETYL ALPHA MANNOPYRANOSYLOXY)ETHYL]AMIDE; CYSTEINE 2 [2 (ALPHA MANNOPYRANOSYLOXY)ETHYL]AMIDE; CYSTEINE [2 (2,3,4,6 TETRA O ACETYL ALPHA MANNOPYRANOSYLOXY)ETHYL]AMIDE; CYSTEINE DERIVATIVE; MANNOSIDE; N (FLOUREN 9 YLMETHOXYCARBONYL) O (TERT BUTYL)SERINE BENZYL ESTER; N (FLOUREN 9 YLMETHOXYCARBONYL) O (TERT BUTYL)SERINE ETHYL ESTER; N (FLOUREN 9 YLMETHOXYCARBONYL) O (TERT BUTYL)SERINE PHENYL ESTER; N (FLUOREN 9 YLMETHOXYCARBONYL)(TERT BUTYL)SERINYLCYSTEINE [2 (2,3,4,6 TETRA O ACETYL ALPHA MANNOPYRANOSYLOXY)ETHYL]AMIDE; N (TERT BUTYLOXYCARBONYL)SERINYLCYSTEINE [2 (2,3,4,6 TETRA O ACETYL ALPHA MANNOPYRANOSYLOXY)ETHYL]AMIDE; N [[4 (ALPHA MANNOPYRANOSYLOXY)PHENYL ACETYL]][3 (ALPHA MANNOPYRANOSYLOXY)PROPYL]CYSTEINE; N [[4 (ALPHA MANNOPYRANOSYLOXY)PHENYL ACETYL]][3 (ALPHA MANNOPYRANOSYLOXY)PROPYL]CYSTEINE ETHYL ESTER; N [[4 (ALPHA MANNOPYRANOSYLOXY)PHENYL ACETYL]][3 (ALPHA MANNOPYRANOSYLOXY)PROPYL]CYSTEINE PHENYL ESTER; N [[4 (ALPHA MANNOPYRANOSYLOXY)PHENYL]ACETYL]CYSTEINE [2 (ALPHA MANNOPYRANOSYLOXY)ETHYL]AMIDE; N,N' [N [[4 (ALPHA MANNOPYRANOSYLOXY)PHENYL]ACETYL][3 (ALPHA MANNOPYRANOSYLOXY)PROPYL]CYSTEINYL]CYSTINE 2 [2 (ALPHA MANNOPYRANOSYLOXY)ETHYL]AMIDE; SERINE DERIVATIVE; THIOESTER; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL PROCEDURES; CHEMICAL REACTION; CHEMICAL STRUCTURE; DERIVATIZATION; DIMERIZATION; EPIMERIZATION; GLYCOSYLATION; NATIVE CHEMICAL LIGATION; OXIDATION; PURIFICATION; SYNTHESIS;

EID: 77956469199     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1258157     Document Type: Article

References (29)

1. Becker C F. W., Liu X, Olschewski D, Castelli R, Seidel R, Seeberger P H., Angew. Chem. Int. Ed. 2008 47 8215; Angew. Chem. 2008, 120, 8338
2. Dawson P E., Muir T W., Clark-Lewis I, Kent S B., Science 1994 266 776
3. Brik A, Ficht S, Wong C.-H, Curr. Opin. Chem. Biol. 2006 10 638
4. Hackenberger C P. R., Schwarzer D, Angew. Chem. Int. Ed. 2008 47 10030; Angew. Chem. 2008, 120, 10182
5. Gamblin D P., Scanlan E M., Davis B G., Chem. Rev. 2009 109 131
6. Wieland T, Bokelmann E, Bauer L, Lang H U., Lau H, Justus Liebigs Ann. Chem. 1953 583 129
7. van Baal I, Malda H, Synowsky S A., van Dongen J L. J., Hackeng T M., Merkx M, Meijer E W., Angew. Chem. Int. Ed. 2005 44 5052; Angew. Chem. 2005, 117, 5180
8. Dirksen A, Meijer E W., Adriaens W, Hackeng T M., Chem. Commun. 2006 1667
9. Zhong W, Skwarczynski M, Fujita Y, Simerska P, Good M F., Toth I, Aust. J. Chem. 2009 9 993
10. Moyle P M., Hari Y, Huang N, Olive C, Good M F., Toth I, Tetrahedron Lett. 2007 48 4965
11. Lempens E H. M., Helms B A., Bayles A R., Merkx M, Meijer E W., Eur. J. Org. Chem. 2010 111
12. Röckendorf N, Lindhorst T K., Top. Curr. Chem. 2001 217 201
13. Pieters R J., Org. Biomol. Chem. 2009 7 2013
14. Lahmann M, Top. Curr. Chem. 2009 288 17
15. Chabre Y M., Roy R, Adv. Carbohydr. Chem. Biochem. 2010 63 165
16. Chalker J M., Bernardes G J. L., Lin Y A., Davis B G., Chem. Asian J. 2009 4 630
17. Becer C R., Hoogenboom R, Schubert U S., Angew. Chem. Int. Ed. 2009 48 2; Angew. Chem. 2009, 121, 4998
18. Ficht S, Payne R J., Guy R T., Wong C.-H, Chem. Eur. J. 2008 14 3620
19. von Eggelkraut-Gottanka R, Klose A, Beck-Sickinger A G., Beyermann M, Tetrahedron Lett. 2003 44 3551
20. Nagalingam A C., Radford S E., Warriner S L., Synlett 2007 2517
21. Mezo A R., Cheng R P., Imperiali B, J. Am. Chem. Soc. 2001 123 3885
22. Harper J W., Cook R R., Roberts C J., McLaughlin B J., Powers J C., Biochemistry 1984 23 2995
23. Yang H, Liebeskind L S., Org. Lett. 2007 9 2993
24. Derrien D, Midoux P, Petit C, Negre E, Mayer R, Monsigny M, Roche A.-C, Glycoconjugate J. 1989 6 241
25. Jung K.-H, Hoch M, Schmidt R R., Liebigs Ann. Chem. 1989 1099
26. Winnik F M., Carver J P., Krepinsky J J., J. Org. Chem. 1982 47 2701
27. Bien F, Ziegler T, Tetrahedron: Asymmetry 1998 9 781
28. Schierholt A, Shaikh H A., Schmidt-Lassen J, Lindhorst T K., Eur. J. Org. Chem. 2009 3783
29. Schierholt A, Hartmann M, Schwekendiek K, Lindhorst T K., Eur. J. Org. Chem. 2010 3120