Recent progress of sugar amino acids: Synthetic strategies and applications as glycomimetics and peptidomimetics
English
Recent progress of sugar amino acids: Synthetic strategies and applications as glycomimetics and peptidomimetics
-
Key words:
- Sugar amino acids
- / Synthetic strategy
- / Glycomimetics
- / Peptidomimetics
-
-
-
[1] T.K. Chakraborty, P. Srinivasu, S. Tapadar, B.K. Mohan, Sugar amino acids and related molecules: some recent developments, J. Chem. Sci. 116 (2004) 187-207.[1] T.K. Chakraborty, P. Srinivasu, S. Tapadar, B.K. Mohan, Sugar amino acids and related molecules: some recent developments, J. Chem. Sci. 116 (2004) 187-207.
-
[2] T.K. Chakraborty, P. Srinivasu, S. Tapadar, B.K. Mohan, Sugar amino acids in designing new molecules, Glycoconj. J. 22 (2005) 83-93.[2] T.K. Chakraborty, P. Srinivasu, S. Tapadar, B.K. Mohan, Sugar amino acids in designing new molecules, Glycoconj. J. 22 (2005) 83-93.
-
[3] S.A.W. Gruner, E. Locardi, E. Lohof, H. Kessler, Carbohydrate-based mimetics in drug design: sugar amino acids and carbohydrate scaffolds, Chem. Rev. 102 (2002) 491-514.[3] S.A.W. Gruner, E. Locardi, E. Lohof, H. Kessler, Carbohydrate-based mimetics in drug design: sugar amino acids and carbohydrate scaffolds, Chem. Rev. 102 (2002) 491-514.
-
[4] X. Chen, A. Varki, Advances in the biology and chemistry of sialic acids, ACS Chem. Biol. 5 (2010) 163-176.[4] X. Chen, A. Varki, Advances in the biology and chemistry of sialic acids, ACS Chem. Biol. 5 (2010) 163-176.
-
[5] J. Gervay-Hague, J.T.M. Weathers, Pyranosyl sugar amino acid conjugates: their biological origins, synthetic preparations, and structural characterization, J. Carbohydr. Chem. 21 (2002) 867-910.[5] J. Gervay-Hague, J.T.M. Weathers, Pyranosyl sugar amino acid conjugates: their biological origins, synthetic preparations, and structural characterization, J. Carbohydr. Chem. 21 (2002) 867-910.
-
[6] M.T. Migawa, L.M. Risen, R.H. Griffey, E.E. Swayze, An efficient synthesis of gougerotin and related analogues using solid-and solution-phase methodology, Org. Lett. 7 (2005) 3429-3432.[6] M.T. Migawa, L.M. Risen, R.H. Griffey, E.E. Swayze, An efficient synthesis of gougerotin and related analogues using solid-and solution-phase methodology, Org. Lett. 7 (2005) 3429-3432.
-
[7] A. Maciejewska, J. Lukasiewicz, T. Niedziela, Z. Szewczukc, C. Lugowski, Structural analysis of the O-specific polysaccharide isolated from Plesiomonas shigelloides O51 lipopolysaccharide, Carbohydr. Res. 344 (2009) 894-900.[7] A. Maciejewska, J. Lukasiewicz, T. Niedziela, Z. Szewczukc, C. Lugowski, Structural analysis of the O-specific polysaccharide isolated from Plesiomonas shigelloides O51 lipopolysaccharide, Carbohydr. Res. 344 (2009) 894-900.
-
[8] G.Q. Niu, H.R. Tan, Nucleoside antibiotics: biosynthesis, regulation, and biotechnology, Trends Microbiol. 23 (2015) 110-119.[8] G.Q. Niu, H.R. Tan, Nucleoside antibiotics: biosynthesis, regulation, and biotechnology, Trends Microbiol. 23 (2015) 110-119.
-
[9] M. Risseeuw, M. Overhand, G.W.J. Fleet, M.I. Simone, A compendium of cyclic sugar amino acids and their carbocyclic and heterocyclic nitrogen analogues, Amino Acids 45 (2013) 613-689.[9] M. Risseeuw, M. Overhand, G.W.J. Fleet, M.I. Simone, A compendium of cyclic sugar amino acids and their carbocyclic and heterocyclic nitrogen analogues, Amino Acids 45 (2013) 613-689.
-
[10] M. Nakajima, K. Itoi, Y. Takamatsu, et al., Hydantocidin: a new compound with herbicidal activity from Streptomyces hygroscopicus, J. Antibiot. (Tokyo) 44 (1991) 293-300.[10] M. Nakajima, K. Itoi, Y. Takamatsu, et al., Hydantocidin: a new compound with herbicidal activity from Streptomyces hygroscopicus, J. Antibiot. (Tokyo) 44 (1991) 293-300.
-
[11] D. Tuwalska, A. Sikorski, B. Liberek, Synthesis and geometry of methyl (methyl 4-O-acetyl-3-azido-2,3-dideoxy-α/β-D-arabino-and -α/β-D-ribo-hexopyranosid) urinates, Carbohydr. Res. 343 (2008) 404-411.[11] D. Tuwalska, A. Sikorski, B. Liberek, Synthesis and geometry of methyl (methyl 4-O-acetyl-3-azido-2,3-dideoxy-α/β-D-arabino-and -α/β-D-ribo-hexopyranosid) urinates, Carbohydr. Res. 343 (2008) 404-411.
-
[12] D. Tuwalska, J. Sienkiewicz, B. Liberek, Synthesis and conformational analysis of methyl 3-amino-2, 3-dideoxyhexopyranosiduronic acids, new sugar amino acids, and their diglycotides, Carbohydr. Res. 343 (2008) 1142-1152.[12] D. Tuwalska, J. Sienkiewicz, B. Liberek, Synthesis and conformational analysis of methyl 3-amino-2, 3-dideoxyhexopyranosiduronic acids, new sugar amino acids, and their diglycotides, Carbohydr. Res. 343 (2008) 1142-1152.
-
[13] P. Phiasivongsa, J. Gallagher, C.N. Chen, et al., Palladium-charcoal-catalyzed reduction of tri-O-acetyl-β-L-fucopyranosyl cyanide: a route to small cluster oligosaccharide mimetics (SCOMs), Org. Lett. 4 (2002) 4587-4590.[13] P. Phiasivongsa, J. Gallagher, C.N. Chen, et al., Palladium-charcoal-catalyzed reduction of tri-O-acetyl-β-L-fucopyranosyl cyanide: a route to small cluster oligosaccharide mimetics (SCOMs), Org. Lett. 4 (2002) 4587-4590.
-
[14] E. Lohof, E. Planker, C.Mang, et al., Carbohydrate derivatives for use in drug design: cyclicαv-selective RGD peptides, Angew. Chem. Int. Ed. Engl. 39 (2000) 2761-2764.[14] E. Lohof, E. Planker, C.Mang, et al., Carbohydrate derivatives for use in drug design: cyclicαv-selective RGD peptides, Angew. Chem. Int. Ed. Engl. 39 (2000) 2761-2764.
-
[15] A.E.J. de Nooy, A.C. Besemer, et al., Selective oxidation of primary alcohols mediated by nitroxyl radical in aqueous solution. Kinetics and mechanism, Tetrahedron 51 (1995) 8023-8032.[15] A.E.J. de Nooy, A.C. Besemer, et al., Selective oxidation of primary alcohols mediated by nitroxyl radical in aqueous solution. Kinetics and mechanism, Tetrahedron 51 (1995) 8023-8032.
-
[16] E. Kallin, Use of glycosylamines in preparation of oligosaccharide polyacrylamide copolymers, Methods Enzymol. 242 (1994) 221-226.[16] E. Kallin, Use of glycosylamines in preparation of oligosaccharide polyacrylamide copolymers, Methods Enzymol. 242 (1994) 221-226.
-
[17] L.Q. Ying, J. Gervay-Hague, Synthesis of N-(fluoren-9-ylmethoxycarbonyl)glycopyranosylamine uronic acids, Carbohydr. Res. 339 (2004) 367-375.[17] L.Q. Ying, J. Gervay-Hague, Synthesis of N-(fluoren-9-ylmethoxycarbonyl)glycopyranosylamine uronic acids, Carbohydr. Res. 339 (2004) 367-375.
-
[18] L.Q. Ying, J. Gervay-Hague, General methods for the synthesis of glycopyranosyluronic acid azides, Carbohydr. Res. 338 (2003) 835-841.[18] L.Q. Ying, J. Gervay-Hague, General methods for the synthesis of glycopyranosyluronic acid azides, Carbohydr. Res. 338 (2003) 835-841.
-
[19] J.P. McDevitt, P.T. Lansbury Jr., Glycosamino acids: new building blocks for combinatorial synthesis, J. Am. Chem. Soc. 118 (1996) 3818-3828.[19] J.P. McDevitt, P.T. Lansbury Jr., Glycosamino acids: new building blocks for combinatorial synthesis, J. Am. Chem. Soc. 118 (1996) 3818-3828.
-
[20] (a) R.M. van Well, H.S. Overkleeft, M. Overhand, et al., Parallel synthesis of cyclic sugar amino acid/amino acid hybrid molecules, Tetrahedron Lett. 41 (2000) 9331-9335; (b) R.M. van Well, L. Marinelli, K. Erkelens, et al., Synthesis and structural analysis of cyclic oligomers consisting of furanoid and pyranoid e-sugar amino acids, Eur. J. Org. Chem. 12 (2003) 2303-2313.[20] (a) R.M. van Well, H.S. Overkleeft, M. Overhand, et al., Parallel synthesis of cyclic sugar amino acid/amino acid hybrid molecules, Tetrahedron Lett. 41 (2000) 9331-9335; (b) R.M. van Well, L. Marinelli, K. Erkelens, et al., Synthesis and structural analysis of cyclic oligomers consisting of furanoid and pyranoid e-sugar amino acids, Eur. J. Org. Chem. 12 (2003) 2303-2313.
-
[21] E.G. von Roedern, E. Lohof, G. Hessler, M. Hoffmann, H. Kessler, Synthesis and conformational analysis of linear and cyclic peptides containing sugar amino acids, J. Am. Chem. Soc. 118 (1996) 10156-10167.[21] E.G. von Roedern, E. Lohof, G. Hessler, M. Hoffmann, H. Kessler, Synthesis and conformational analysis of linear and cyclic peptides containing sugar amino acids, J. Am. Chem. Soc. 118 (1996) 10156-10167.
-
[22] Y. Suhara, M. Kurihara, A. Kittaka, Y. Ichikawa, Efficient synthesis of carbopeptoid oligomers: insight into mimicry of b-peptide, Tetrahedron 62 (2006) 8207-8217.[22] Y. Suhara, M. Kurihara, A. Kittaka, Y. Ichikawa, Efficient synthesis of carbopeptoid oligomers: insight into mimicry of b-peptide, Tetrahedron 62 (2006) 8207-8217.
-
[23] R.W. Myers, L.C. Lee, Synthesis and characterization of some anomeric pairs of per-O-acetylated aldohexopyranosyl cyanides (per-O-acetylated 2,6-anhydroheptononitriles). On the reaction of per-O-acetylaldohexopyranosyl bromides with mercuric cyanide in nitromethane, Carbohydr. Res. 132 (1984) 61-82.[23] R.W. Myers, L.C. Lee, Synthesis and characterization of some anomeric pairs of per-O-acetylated aldohexopyranosyl cyanides (per-O-acetylated 2,6-anhydroheptononitriles). On the reaction of per-O-acetylaldohexopyranosyl bromides with mercuric cyanide in nitromethane, Carbohydr. Res. 132 (1984) 61-82.
-
[24] T.K. Chakraborty, S. Ghosh, S. Jayaprakash, Sugar amino acids and their uses in designing bioactive molecules, Curr. Med. Chem. 9 (2002) 421-435.[24] T.K. Chakraborty, S. Ghosh, S. Jayaprakash, Sugar amino acids and their uses in designing bioactive molecules, Curr. Med. Chem. 9 (2002) 421-435.
-
[25] F. Schweizer, Unusual amino acids accessed through sugar-amino acid hybrids and incorporation into biologically active peptides, Trends Glycosci. Glycotechnol. 15 (2003) 315-328.[25] F. Schweizer, Unusual amino acids accessed through sugar-amino acid hybrids and incorporation into biologically active peptides, Trends Glycosci. Glycotechnol. 15 (2003) 315-328.
-
[26] Y. Suhara, Y. Yamaguchi, B. Collins, et al., Oligomers of glycamino acid, Bioorg. Med. Chem. 10 (2002) 1999-2013.[26] Y. Suhara, Y. Yamaguchi, B. Collins, et al., Oligomers of glycamino acid, Bioorg. Med. Chem. 10 (2002) 1999-2013.
-
[27] Z. Song, X.P. He, G.R. Chen, J. Xie, 6-O-amino-2-O-carboxymethyl glucopyranoside as novel glycoaminoxy acid building block for the construction of oligosaccharide mimetics, Synthesis 17 (2011) 2761-2766.[27] Z. Song, X.P. He, G.R. Chen, J. Xie, 6-O-amino-2-O-carboxymethyl glucopyranoside as novel glycoaminoxy acid building block for the construction of oligosaccharide mimetics, Synthesis 17 (2011) 2761-2766.
-
[28] M.I. Simone, A.A. Edwards, G.E. Tranter, G.W.J. Fleet, C-3 branched d-3, 5-cis-and trans-THF sugar amino acids: synthesis of the first generation of branched homooligomers, Amino Acids 41 (2011) 643-661.[28] M.I. Simone, A.A. Edwards, G.E. Tranter, G.W.J. Fleet, C-3 branched d-3, 5-cis-and trans-THF sugar amino acids: synthesis of the first generation of branched homooligomers, Amino Acids 41 (2011) 643-661.
-
[29] M. Mé nand, J.C. Blais, L. Hamon, J.M. Valé ry, J. Xie, Synthesis of orthogonally protected cyclic homooligomers from sugar amino acids, J. Org. Chem. 70 (2005) 4423-4430.[29] M. Mé nand, J.C. Blais, L. Hamon, J.M. Valé ry, J. Xie, Synthesis of orthogonally protected cyclic homooligomers from sugar amino acids, J. Org. Chem. 70 (2005) 4423-4430.
-
[30] A. Feher-Voelger, J. Borges-Gonzá lez, R. Carrillo Dr, et al., Synthesis and conformational analysis of cyclic homooligomers from pyranoid e-sugar amino acids, Chem. Eur. J. 20 (2014) 4007-4022.[30] A. Feher-Voelger, J. Borges-Gonzá lez, R. Carrillo Dr, et al., Synthesis and conformational analysis of cyclic homooligomers from pyranoid e-sugar amino acids, Chem. Eur. J. 20 (2014) 4007-4022.
-
[31] J.P. Saludes, J.B. Ames, J. Gervay-Hague, Synthesis and structural characterization of sialic acid-glutamic acid hybrid foldamers as conformational surrogates of a-2, 8-linked polysialic acid, J. Am. Chem. Soc. 131 (2009) 5495-5505.[31] J.P. Saludes, J.B. Ames, J. Gervay-Hague, Synthesis and structural characterization of sialic acid-glutamic acid hybrid foldamers as conformational surrogates of a-2, 8-linked polysialic acid, J. Am. Chem. Soc. 131 (2009) 5495-5505.
-
[32] M.D.P. Risseeuw, B.I. Florea, G.A. van der Marel, H.S. Overkleeft, M. Overhand, Sugar amino acid based peptide epoxyketones as potential proteasome inhibitors, Bioorg. Chem. 38 (2010) 202-209.[32] M.D.P. Risseeuw, B.I. Florea, G.A. van der Marel, H.S. Overkleeft, M. Overhand, Sugar amino acid based peptide epoxyketones as potential proteasome inhibitors, Bioorg. Chem. 38 (2010) 202-209.
-
[33] A. Siriwardena, K.K. Pulukuri, P.S. Kandiyal, et al., Sugar-modified foldamers as conformationally defined and biologically distinct glycopeptide mimics, Angew. Chem. Int. Ed. 52 (2013) 10221-10226.[33] A. Siriwardena, K.K. Pulukuri, P.S. Kandiyal, et al., Sugar-modified foldamers as conformationally defined and biologically distinct glycopeptide mimics, Angew. Chem. Int. Ed. 52 (2013) 10221-10226.
-
[34] (a) R.M. van Well, L. Marinelli, C. Altona, et al., Conformational analysis of furanoid ε-sugar amino acid containing cyclic peptides by NMR spectroscopy, molecular dynamics simulation, and X-ray crystallography: evidence for a novel turn structure, J. Am. Chem. Soc. 125 (2003) 10822-10829; (b) R.M. van Well, H.S. Overkleeft, G.A. van der Marel, et al., Solid-phase synthesis of cyclic RGD-furanoid sugar amino acid peptides as integrin inhibitors, Bioorg. Med. Chem. Lett. 13 (2003) 331-334.[34] (a) R.M. van Well, L. Marinelli, C. Altona, et al., Conformational analysis of furanoid ε-sugar amino acid containing cyclic peptides by NMR spectroscopy, molecular dynamics simulation, and X-ray crystallography: evidence for a novel turn structure, J. Am. Chem. Soc. 125 (2003) 10822-10829; (b) R.M. van Well, H.S. Overkleeft, G.A. van der Marel, et al., Solid-phase synthesis of cyclic RGD-furanoid sugar amino acid peptides as integrin inhibitors, Bioorg. Med. Chem. Lett. 13 (2003) 331-334.
-
[35] T.K. Chakraborty, D. Koley, R. Ravi, et al., Synthesis, conformational analysis and biological studies of cyclic cationic antimicrobial peptides containing sugar amino acids, J. Org. Chem. 73 (2008) 8731-8744.[35] T.K. Chakraborty, D. Koley, R. Ravi, et al., Synthesis, conformational analysis and biological studies of cyclic cationic antimicrobial peptides containing sugar amino acids, J. Org. Chem. 73 (2008) 8731-8744.
-
[36] A.D. Knijnenburg, A.W. Tuin, E. Spalburg, et al., Exploring the conformational and biological versatility of β-turn-modified gramicidin S by using sugar amino acid homologues that vary in ring size, Chem. Eur. J. 17 (2011) 3995-4004.[36] A.D. Knijnenburg, A.W. Tuin, E. Spalburg, et al., Exploring the conformational and biological versatility of β-turn-modified gramicidin S by using sugar amino acid homologues that vary in ring size, Chem. Eur. J. 17 (2011) 3995-4004.
-
[37] S. Gajendra, G. Uttam, P. Sudip, et al., βγ-fused turn structures in sugar amino acid (SAA) containing cyclic tetrapeptides with a3d architecture, Tetrahedron 70 (2014) 7681-7685.[37] S. Gajendra, G. Uttam, P. Sudip, et al., βγ-fused turn structures in sugar amino acid (SAA) containing cyclic tetrapeptides with a3d architecture, Tetrahedron 70 (2014) 7681-7685.
-
-
扫一扫看文章
计量
- PDF下载量: 0
- 文章访问数: 1556
- HTML全文浏览量: 25

下载: