Synthesis of unnatural <i>N</i>-glycosyl <i>α</i>-amino acids <i>via</i> Petasis reaction

注册 English

Synthesis of unnatural N-glycosyl α-amino acids via Petasis reaction

Chuan-Zhou Tao , Zhong-Tang Zhang , Jian-Wei Wu , Rong-Hua Li , Zhi-Ling Cao

Citation: Chuan-Zhou Tao, Zhong-Tang Zhang, Jian-Wei Wu, Rong-Hua Li, Zhi-Ling Cao. Synthesis of unnatural N-glycosyl α-amino acids via Petasis reaction[J]. Chinese Chemical Letters, 2014, 25(4): 532-534. doi: 10.1016/j.cclet.2014.01.035 shu

shu

Synthesis of unnatural N-glycosyl α-amino acids via Petasis reaction

通讯作者: Chuan-Zhou Tao,

基金项目:
We are grateful to the Natural Science Foundation of Jiangsu Province (No. BK20130404) (No. BK20130404)

Technological Research Project of Lianyungang (No. CG1303) (No. CG1303)

摘要: A convenient and efficient protocol for the synthesis of unnatural N-glycosyl α-amino acids was developed. Condensation of 1,3,4,6-tetra-O-actyl-β-D-glucosamine hydrochloride, alkenyl boronic acid, and glyoxylic acid was achieved in CH₂Cl₂ to give the derivatives of 2-(N-glycosyl)aminobut-3-enoic acid which may find applications in glycobiology research and medicinal chemistry.

关键词:

English

Synthesis of unnatural N-glycosyl α-amino acids via Petasis reaction

1.
a School of Chemical Engineering, Huaihai Institute of Technology, Lianyungang 222005, China;
2.
b Jiangsu Marine Resources Development Research Institute, Lianyungang 222005, China

Corresponding author: Chuan-Zhou Tao,

Received Date: 17 October 2013
Available Online: 25 January 2014
Fund Project:

Abstract: A convenient and efficient protocol for the synthesis of unnatural N-glycosyl α-amino acids was developed. Condensation of 1,3,4,6-tetra-O-actyl-β-D-glucosamine hydrochloride, alkenyl boronic acid, and glyoxylic acid was achieved in CH₂Cl₂ to give the derivatives of 2-(N-glycosyl)aminobut-3-enoic acid which may find applications in glycobiology research and medicinal chemistry.

Key words:

1. [1] 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.[1] 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.
2. [2] P.M. St. Hilaire, T.L. Lowary, M. Meldal, K. Bock, Oligosaccharide mimetics obtained by novel, rapid screening of carboxylic acid encoded glycopeptide libraries, J. Am. Chem. Soc. 120 (1998) 13312-13320.[2] P.M. St. Hilaire, T.L. Lowary, M. Meldal, K. Bock, Oligosaccharide mimetics obtained by novel, rapid screening of carboxylic acid encoded glycopeptide libraries, J. Am. Chem. Soc. 120 (1998) 13312-13320.
3. [3] L. Jobron, G. Hummel, Solid-phase synthesis of unprotected N-glycopeptide building blocks for SPOT synthesis of N-linked glycopeptides, Angew. Chem. Int. Ed. 39 (2000) 1621-1624.[3] L. Jobron, G. Hummel, Solid-phase synthesis of unprotected N-glycopeptide building blocks for SPOT synthesis of N-linked glycopeptides, Angew. Chem. Int. Ed. 39 (2000) 1621-1624.
4. [4] L. Liu, C.S. Bennett, C.H. Wong, Advances in glycoprotein synthesis, Chem. Commun. (2006) 21-33.[4] L. Liu, C.S. Bennett, C.H. Wong, Advances in glycoprotein synthesis, Chem. Commun. (2006) 21-33.
5. [5] D.P. Gamblin, E.M. Scanlan, B.G. Davis, Glycoprotein synthesis: an update, Chem. Rev. 109 (2009) 131-163.[5] D.P. Gamblin, E.M. Scanlan, B.G. Davis, Glycoprotein synthesis: an update, Chem. Rev. 109 (2009) 131-163.
6. [6] G.M. Fang, Y.M. Li, F. Shen, et al., Protein chemical synthesis by ligation of peptide hydrazides, Angew. Chem. Int. Ed. 50 (2011) 7645-7649.[6] G.M. Fang, Y.M. Li, F. Shen, et al., Protein chemical synthesis by ligation of peptide hydrazides, Angew. Chem. Int. Ed. 50 (2011) 7645-7649.
7. [7] Y. Hajihara, M. Izumi, K. Hirano, et al., Elucidating the function of complex-type oligosaccharides by use of chemical synthesis of homogeneous glycoproteins, Isr. J. Chem. 51 (2011) 917-929.[7] Y. Hajihara, M. Izumi, K. Hirano, et al., Elucidating the function of complex-type oligosaccharides by use of chemical synthesis of homogeneous glycoproteins, Isr. J. Chem. 51 (2011) 917-929.
8. [8] J.S. Zheng, H.N. Chang, F.L. Wang, L. Liu, Fmoc synthesis of peptide thioesters without post-chain-assembly manipulation, J. Am. Chem. Soc. 133 (2011) 11080-11083.[8] J.S. Zheng, H.N. Chang, F.L. Wang, L. Liu, Fmoc synthesis of peptide thioesters without post-chain-assembly manipulation, J. Am. Chem. Soc. 133 (2011) 11080-11083.
9. [9] V.L. Campo, I. Carvalho, S. Allman, B.G. Davis, R.A. Field, Chemical and chemoenzymatic synthesis of glycosyl-amino acids and glycopeptides related to Trypanosoma cruzi mucins, Org. Biomol. Chem. 5 (2007) 2645-2657.[9] V.L. Campo, I. Carvalho, S. Allman, B.G. Davis, R.A. Field, Chemical and chemoenzymatic synthesis of glycosyl-amino acids and glycopeptides related to Trypanosoma cruzi mucins, Org. Biomol. Chem. 5 (2007) 2645-2657.
10. [10] A. Nuzzi, A. Massi, A. Dondoni, General synthesis of C-glycosyl amino acids via proline-catalyzed direct electrophilic a-amination of C-glycosylalkyl aldehydes, Org. Lett. 10 (2008) 4485-4488.[10] A. Nuzzi, A. Massi, A. Dondoni, General synthesis of C-glycosyl amino acids via proline-catalyzed direct electrophilic a-amination of C-glycosylalkyl aldehydes, Org. Lett. 10 (2008) 4485-4488.
11. [11] S.B. Cohen, R.L. Halcomb, Application of serine- and threonine-derived cyclic sulfamidates for the preparation of S-linked glycosyl amino acids in solution- and solid-phase peptide synthesis, J. Am. Chem. Soc. 124 (2002) 2534-2543.[11] S.B. Cohen, R.L. Halcomb, Application of serine- and threonine-derived cyclic sulfamidates for the preparation of S-linked glycosyl amino acids in solution- and solid-phase peptide synthesis, J. Am. Chem. Soc. 124 (2002) 2534-2543.
12. [12] A.L. Handlon, B. Fraser-Reid, A convergent strategy for the critical .beta.-linked chitobiosyl-N-glycopeptide core, J. Am. Chem. Soc. 115 (1993) 3796-3797.[12] A.L. Handlon, B. Fraser-Reid, A convergent strategy for the critical .beta.-linked chitobiosyl-N-glycopeptide core, J. Am. Chem. Soc. 115 (1993) 3796-3797.
13. [13] G. Geisberger, E.B. Gyenge, D. Hinger, et al., Chitosan-thioglycolic acid as a versatile antimicrobial agent, Biomacromolecules 14 (2013) 1010-1017.[13] G. Geisberger, E.B. Gyenge, D. Hinger, et al., Chitosan-thioglycolic acid as a versatile antimicrobial agent, Biomacromolecules 14 (2013) 1010-1017.
14. [14] S.M. Srinivas, N.V. Harohally, Improved synthesis of lysine- and argininederived amadori and Heyns products and in vitro measurement of their angiotensin I-converting enzyme inhibitory activity, J. Agric. Food Chem. 60 (2012) 1522-1527.[14] S.M. Srinivas, N.V. Harohally, Improved synthesis of lysine- and argininederived amadori and Heyns products and in vitro measurement of their angiotensin I-converting enzyme inhibitory activity, J. Agric. Food Chem. 60 (2012) 1522-1527.
15. [15] V.V. Mossine, C.L. Barnes, G.V. Glinsky, M.S. Feather, Molecular and crystal structure of N-(2-deoxy-D-aldohexos-2-yl)-glycines (Heyns compounds), Carbohydr. Res. 284 (1996) 11-24.[15] V.V. Mossine, C.L. Barnes, G.V. Glinsky, M.S. Feather, Molecular and crystal structure of N-(2-deoxy-D-aldohexos-2-yl)-glycines (Heyns compounds), Carbohydr. Res. 284 (1996) 11-24.
16. [16] K. Stefan, B. Wolfgang, Metal complexes of biologically important ligands. CXXXI. Pentamethylcyclopentadienyl halfsandwich complexes of rhodium and iridium with glycosyl-alpha-iminocarboxylates as chelate ligands, Z. Naturforsch. B 56 (2001) 62-68.[16] K. Stefan, B. Wolfgang, Metal complexes of biologically important ligands. CXXXI. Pentamethylcyclopentadienyl halfsandwich complexes of rhodium and iridium with glycosyl-alpha-iminocarboxylates as chelate ligands, Z. Naturforsch. B 56 (2001) 62-68.
17. [17] C.Z. Tao, F. Liu, W.W. Liu, et al., Synthesis of N-aryl-D-glucosamines through copper-catalyzed C-N coupling, Tetrahedron Lett. 53 (2012) 7093-7096.[17] C.Z. Tao, F. Liu, W.W. Liu, et al., Synthesis of N-aryl-D-glucosamines through copper-catalyzed C-N coupling, Tetrahedron Lett. 53 (2012) 7093-7096.
18. [18] C.Z. Tao, F. Liu, B. Xu, et al., Copper-catalyzed synthesis of N-aryl-D-glucosamines from arylboronic acids, J. Carbohydr. Chem. 32 (2013) 411-423.[18] C.Z. Tao, F. Liu, B. Xu, et al., Copper-catalyzed synthesis of N-aryl-D-glucosamines from arylboronic acids, J. Carbohydr. Chem. 32 (2013) 411-423.
19. [19] Z.Y. Hong, L. Liu, C.C. Hsu, C.H. Wong, Three-step synthesis of sialic acids and derivatives, Angew. Chem. Int. Ed. 45 (2006) 7417-7421.[19] Z.Y. Hong, L. Liu, C.C. Hsu, C.H. Wong, Three-step synthesis of sialic acids and derivatives, Angew. Chem. Int. Ed. 45 (2006) 7417-7421.
20. [20] Z.Y. Hong, L. Liu, M. Sugiyama, Y. Fu, C.H. Wong, Concise synthesis of iminocyclitols via Petasis-type aminocyclization, J. Am. Chem. Soc. 131 (2009) 8352-8353.[20] Z.Y. Hong, L. Liu, M. Sugiyama, Y. Fu, C.H. Wong, Concise synthesis of iminocyclitols via Petasis-type aminocyclization, J. Am. Chem. Soc. 131 (2009) 8352-8353.
21. [21] H.J. Xu, Y.Q. Zhao, T. Feng, Y.S. Feng, Chan-Lam-type S-arylation of thiols with boronic acids at room temperature, J. Org. Chem. 77 (2012) 2878-2884.[21] H.J. Xu, Y.Q. Zhao, T. Feng, Y.S. Feng, Chan-Lam-type S-arylation of thiols with boronic acids at room temperature, J. Org. Chem. 77 (2012) 2878-2884.
22. [22] J.J. Dai, J.H. Liu, D.F. Luo, L. Liu, Pd-catalysed decarboxylative Suzuki reactions and orthogonal Cu-based O-arylation of aromatic carboxylic acids, Chem. Commun. 47 (2011) 677-679.[22] J.J. Dai, J.H. Liu, D.F. Luo, L. Liu, Pd-catalysed decarboxylative Suzuki reactions and orthogonal Cu-based O-arylation of aromatic carboxylic acids, Chem. Commun. 47 (2011) 677-679.
23. [23] C.T. Yang, Z.Q. Zhang, Y.C. Liu, L. Liu, Copper-catalyzed cross-coupling reaction of organoboron compounds with primary alkyl halides and pseudohalides, Angew. Chem. Int. Ed. 50 (2011) 3904-3907.[23] C.T. Yang, Z.Q. Zhang, Y.C. Liu, L. Liu, Copper-catalyzed cross-coupling reaction of organoboron compounds with primary alkyl halides and pseudohalides, Angew. Chem. Int. Ed. 50 (2011) 3904-3907.
24. [24] P.G.M. Wuts, T.W. Greene (Eds.), Greene's Protective Groups in Organic Synthesis, 4th ed., John Wiley & Sons, New York, 2007.[24] P.G.M. Wuts, T.W. Greene (Eds.), Greene's Protective Groups in Organic Synthesis, 4th ed., John Wiley & Sons, New York, 2007.

WeChat

扫一扫看文章

计量

PDF下载量: 0
文章访问数: 1550
HTML全文浏览量: 35

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

/

下载: 全尺寸图片幻灯片

分享

用微信扫码二维码

分享至好友和朋友圈