Abstract
To meet the growing demands for the development of new molecular entities for discovering new drugs and materials, organic chemists have started working on many new concepts that can help to assimilate knowledge-based structural diversities more efficiently than ever before. Emulating the basic principles followed by Nature to build its vast repertoire of biomolecules, organic chemists are developing many novel multifunctional building blocks and using them to create ‘nature-like’ and yet unnatural organic molecules. Sugar amino acids constitute an important class of such polyfunctional scaffolds where the carboxyl, amino and hydroxyl termini provide an excellent opportunity to organic chemists to create structural diversities akin to Nature’s molecular arsenal. In recent years, sugar amino acids have been used extensively in the area of peptidomimetic studies. Advances made in the area of combinatorial chemistry can provide the necessary technological support for rapid compilations of sugar amino acidbased libraries exploiting the diversities of their carbohydrate frameworks and well-developed solid-phase peptide synthesis methods. This perspective article chronicles some of the recent applications of various sugar amino acids, furan amino acids, pyrrole amino acids etc. and many other related building blocks in wide-ranging peptidomimetic studies
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
Nicolaou K C, Vourloumis D, Winssinger N and Baran P S 2000Angew. Chem., Int. Ed. 39 44
Nicolaou K C and Sorensen E J 1996 InClassics in total synthesis (Weinheim: VCH);
Nicolaou K C and Snyder S A 2003 InClassics in total synthesis II (Weinheim: Wiley-VCH)
Soth M J and Nowick J S 1997Curr. Opin. Chem. Biol. 1 120
Kirshenbaum K, Zuckermann R N and Dill K A 1999Curr. Opin. Struct. Biol. 9 530
Barron A E and Zuckermann R N 1999Curr. Opin. Chem. Biol. 3 681
Mehta G and Singh V 2002Chem. Soc. Rev. 31 324
Rouhi A M 2003C&En. 81 77
Fox M A 1999Acc. Chem. Res. 32 201
Newman D J, Cragg G M and Snader K M 2003J. Nat. Prod. 66 1022
Chakraborty T K, Ghosh S and Jayaprakash S 2002Curr. Med. Chem. 9 421;
Chakraborty T K, Jayaprakash S and Ghosh S 2002Combinatorial Chem. High Throughput Screening 5 373;
Schweizer F 2002Angew. Chem., Int. Ed. 41 230.
Gruner S A W, Locardi E, Lohof E and Kessler H 2002Chem. Rev. 102 491;
Peri F, Cipolla L, Forni E, La Ferla B and Nicotra F 2001Chemtracts Org. Chem. 14 481
Heyns K and Paulsen H 1955Chem. Ber. 88 188
Fuchs E F and Lehmann J 1975Chem. Ber. 108 2254;
Fuchs E F and Lehmann J 1975Carbohydr. Res. 45 135;
Fuchs E F and Lehmann J 1976Carbohydr. Res. 49 267
Graf von Roedern E and Kessler H 1994Angew. Chem., Int. Ed. Engl. 33 687
Graf von Roedern E, Lohof E, Hessler G, Hoffmann M and Kessler H 1996J. Am. Chem. Soc. 118 10156
Chakraborty T K, Jayaprakash S, Diwan P V, Nagaraj R, Jampani S R B and Kunwar A C 1998J. Am. Chem. Soc. 120 12962;
Chakraborty T K, Ghosh S, Jayaprakash S, Sarma J A R P, Ravikanth V, Diwan P V, Nagaraj R and Kunwar A C 2000J. Org. Chem. 65 6441
Poitout L, Merrer Y L and Depezay J-C 1995Tetra-hedron Lett. 36 6887
Coterón J M, Hacket F and Schneider H-J 1996J. Org. Chem. 61 1429
McDonald I K and Thornton J M 1994J. Mol. Biol. 238 777;
Burley S K and Petsko G A 1988Adv. Protein Chem. 39 125
Grotenbreg G M, Timmer M S M, Llamas-Saiz A L, Verdoes M, van der Marel G A, van Raaij M J, Overkleeft H S and Overhand M 2004J. Am. Chem. Soc. 126 3444
Chakraborty T K, Srinivasu P, Madhavendra S S, Kumar S K and Kunwar A C 2004Tetrahedron Lett. 45 3573
Smith M D, Claridge T D W, Sansom M S P and Fleet G W J 2003Org. Biomol. Chem. 1 3647
Davis A P and Wareham R S 1999Angew. Chem., tInt. Ed. 38 2978
Chakraborty T K, Jayaprakash S, Srinivasu P, Madhavendra S S, Sankar A R and Kunwar A C 2002Tetrahedron 58 2853
Chakraborty T K, Ghosh S, Rao M H V R, Kunwar A C, Cho H and Ghosh A K 2000Tetrahedron Lett. 41 10121
Chakraborty T K, Srinivasu P, Kumar S K and Kunwar A C 2002J. Org. Chem. 67 2093
Stöckle M, Voll G, Günther R, Lohof E, Locardi E, Gruner S and Kessler H 2002Org. Lett. 4 2501
Gellman S H 1997Acc. Chem. Res. 31 173
Hill D J, Mio M J, Prince R B, Hughes T S and Moore J S 2001Chem. Rev. 101 3893
Chakraborty T K, Srinivasu P, Bikshapathy E, Nagaraj R, Vairamani M, Kumar S K and Kunwar A C 2003J. Org. Chem. 68 6257
Locardi E, Stöckle M, Gruner S and Kessler H 2001J.Am. Chem. Soc. 123 8189
van Well R M, Overkleeft H S, van Boom J H, Coop A, Wang J B, Wang H, van der Marel G A and Over-hand M 2003Eur. J. Org. Chem. 1704, and references cited therein
Gruner SAW, Truffault V, Voll G, Locardi E, Stöckle M and Kessler H 2002Chem. Eur. J. 8 4365
Gruner SAW, Kéri G, Schwab R, Venetianer A and Kessler H 2001Org. Lett. 3 3723
van Well R M, Marinelli M, Erkelens K, van der Marel G A, Lavecchia A, Overkleeft H S, van Boom J H, Kessler H and Overhand M 2003Eur. J. Org. Chem. 2303
van Well R M, Overkleeft H S, van der Marel G A, Bruss D, Thibault G, de Groot P G, van Boom J H and Overhand M 2003Bioorg. Med. Chem. 13 331;
van Well R M, Overkleeft H S, Overhand M, Carstenen E V, van der Marel G A and van Boom J H 2000Tetrahedron Lett. 41 9331
van Well R M, Marinelli L, Altona C, Erkelens K, Siegal G, van Raaij M, Liamas-Saiz A, Kessler H, Novellino E, Lavecchia A, van Boom J H and Overhand M 2003J. Am. Chem. Soc. 125 10822
van Well R M, Meijer M E A, Overkleeft H S, van Boom J H, van der Marel G A and Overhand M 2003Tetrahedron 59 2423
Chakraborty T K, Ghosh A, Nagaraj R, Sankar A R and Kunwar A C 2001Tetrahedron 57 9169
Chakraborty T K, Tapadar S and Kumar S K 2002Tetrahedron Lett. 43 1317
Chakraborty T K, Mohan B K, Kumar S K and Kunwar A C 2002Tetrahedron Lett. 43 2589
Chakraborty T K, Mohan B K, Kumar S K and Kunwar A C 2003Tetrahedron Lett. 44 471
Bonauer C, Zabel M and König B 2004Org. Lett. 6 1349
Suhara Y, Yamaguchi Y, Collins B, Schnaar R L, Yanagishita M, Hildreth J E K, Shimada I and Ichikawa Y 2002Bioorg. Med. Chem. 10 1999
Ying L and Gervay-Hague J 2004Carbohydrate Res. 339 367
Gregar T Q and Gervay-Hague J 2004J. Org. Chem. 69 1001
Edwards A A, Ichihara O, Murfin S, Wilkes R, Whittaker M, Watkin D J and Fleet G W J 2004J. Comb. Chem. 6 230
Mazur A W, Kulesza A, Mishra R A, Cross-Doersen D, Russell A F and Ebetino F H 2003Bioorg. Med. Chem. 11 3053;
Kulesza A, Ebetino F H, Mishra R K, Cross-Doersen D and Mazur A W 2003Org. Lett. 5 1163
Vescovi A, Knoll A and Koert U 2003Org. Biomol. Chem. 1 2983
Hunter D F A and Fleet G W J 2003Tetrahedron: Asymmetry 14 3831
Mayes B A, Stetz R J E, Watterson M P, Edwards A A, Ansell C W G, Tranter G E and Fleet G W J 2004Tetrahedron: Asymmetry 15 627
Mayes B A, Stetz R J E, Ansell C W G and Fleet G W J 2004Tetrahedron Lett. 45 153
Mayes B A, Simon L, Watkin D J, Ansell C W G and Fleet G W J 2004Tetrahedron Lett. 45 157
Mayes B A, Cowley A R, Ansell C W G and Fleet G W J 2004Tetrahedron Lett. 45 163
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Chakraborty, T.K., Srinivasu, P., Tapadar, S. et al. Sugar amino acids and related molecules: Some recent developments. J Chem Sci 116, 187–207 (2004). https://doi.org/10.1007/BF02708268
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF02708268