3-Azidoazetidines as the first scaffolds for β-amino azetidine carboxylic acid peptidomimetics: azetidine iminosugars containing an acetamido group do not inhibit β-N-acetylhexosaminidases

被引：3
作者：
Liu, Zilei [1 ]
Jenkinson, Sarah F. [1 ]
Kato, Atsushi [2 ]
Nakagawa, Shinpei [2 ]
Wormald, Mark R. [3 ]
Yu, Chu-Yi [4 ,5 ]
Fleet, George W. J. [1 ,5 ]
机构：
[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England
[2] Toyama Univ, Dept Hosp Pharm, Toyama 9300194, Japan
[3] Univ Oxford, Dept Biochem, Glycobiol Inst, Oxford OX1 3QU, England
[4] Chinese Acad Sci, Inst Chem, CAS Key Lab Mol Recognit & Funct, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China
[5] Jiangxi Normal Univ, Natl Engn Res Ctr Carbohydrate Synth, Nanchang 330022, Peoples R China
来源：
TETRAHEDRON-ASYMMETRY | 2016年 / 27卷 / 17-18期
关键词：
EFFICIENT S(N)2 REACTIONS; AZETIDINE-2-CARBOXYLIC ACID; BIOLOGICAL EVALUATION; HEXOSAMINIDASE INHIBITORS; CONVENIENT SYNTHESIS; ANTIBIOTIC OXETIN; D-GLUCOSAMINIDASE; OXETANE RINGS; L-RHAMNOSE; D-GLUCOSE;
D O I：
10.1016/j.tetasy.2016.08.001
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Stable amides and oligopeptides derived from methyl trans,trans-3-azido-4-hydroxymethyl-L-azetidine carboxylate, prepared in 19% yield from diacetone allose, is the first example of a beta-amino-azetidine carboxylic acid incorporated into peptidomimetics and provides a scaffold for investigating secondary structure induced by a novel beta-amino acid. A number of azetidine iminosugars containing a NHAc substituent were prepared but none of them were beta-N-acetylhexosaminidase inhibitors. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码：872 / 881
页数：10
相关论文
共 68 条
  • [1] Cytoprotective pyridinol antioxidants as potential therapeutic agents for neurodegenerative and mitochondrial diseases
    Alam, Mohammad Parvez
    Khdour, Omar M.
    Arce, Pablo M.
    Chen, Yana
    Roy, Basab
    Johnson, Walter G.
    Dey, Sriloy
    Hecht, Sidney M.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2014, 22 (17) : 4935 - 4947
  • [2] Synthesis of pyrrolidine-based analogues of 2-acetamidosugars as N-acetyl-D-glucosaminidase inhibitors
    Anh Tuan Tran
    Luo, Bo
    Jagadeesh, Yerri
    Auberger, Nicolas
    Desire, Jerome
    Nakagawa, Shinpei
    Kato, Atsushi
    Zhang, Yongmin
    Bleriot, Yves
    Sollogoub, Matthieu
    [J]. CARBOHYDRATE RESEARCH, 2015, 409 : 56 - 62
  • [3] THE STRUCTURE OF NAGSTATIN, A NEW INHIBITOR OF N-ACETYL-BETA-D-GLUCOSAMINIDASE
    AOYAMA, T
    NAGANAWA, H
    SUDA, H
    UOTANI, K
    AOYAGI, T
    TAKEUCHI, T
    [J]. JOURNAL OF ANTIBIOTICS, 1992, 45 (09) : 1557 - 1558
  • [4] Synthesis from D-Altrose of (5R,6R,7R,8S)-5,7-Dihydroxy-8-hydroxymethylconidine and 2,4-Dideoxy-2,4-imino-D-glucitol, Azetidine Analogues of Swainsonine and 1,4-Dideoxy-1,4-imino-D-mannitol
    Araujo, Noelia
    Jenkinson, Sarah F.
    Martinez, R. Fernando
    Glawar, Andreas F. G.
    Wormald, Mark R.
    Butters, Terry D.
    Nakagawa, Shinpei
    Adachi, Isao
    Kato, Atsushi
    Yoshihara, Akihide
    Akimitsu, Kazuya
    Izumori, Ken
    Fleet, George W. J.
    [J]. ORGANIC LETTERS, 2012, 14 (16) : 4174 - 4177
  • [5] AUSTIN GN, 1987, TETRAHEDRON, V43, P3095
  • [6] Nine of 16 Stereoisomeric Polyhydroxylated Proline Amides Are Potent β-N-Acetylhexosaminidase Inhibitors
    Ayers, Benjamin J.
    Glawar, Andreas F. G.
    Martinez, R. Fernando
    Ngo, Nigel
    Liu, Zilei
    Fleet, George W. J.
    Butters, Terry D.
    Nash, Robert J.
    Yu, Chu-Yi
    Wormald, Mark R.
    Nakagawa, Shinpei
    Adachi, Isao
    Kato, Atsushi
    Jenkinson, Sarah F.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (08) : 3398 - 3409
  • [7] Glycosidase Inhibition by All 10 Stereoisomeric 2,5-Dideoxy-2,5-iminohexitols Prepared from the Enantiomers of Glucuronolactone
    Ayers, Benjamin J.
    Ngo, Nigel
    Jenkinson, Sarah F.
    Martinez, R. Fernando
    Shimada, Yousuke
    Adachi, Isao
    Weymouth-Wilson, Alexander C.
    Kato, Atsushi
    Fleet, George W. J.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (18) : 7777 - 7792
  • [8] Cis- and trans-3-Azido-oxetane-2-carboxylate scaffolds:: hexamers of oxetane cis-β-amino acids
    Barker, SF
    Angus, D
    Taillefumier, C
    Probert, MR
    Watkin, DJ
    Watterson, MP
    Claridge, TDW
    Hungerford, NL
    Fleet, GWJ
    [J]. TETRAHEDRON LETTERS, 2001, 42 (25) : 4247 - 4250
  • [9] Synthesis of 2-acetamido-1,2-dideoxy-D-galacto-nojirimycin [DGJNAc] from D-glucuronolactone: the first sub-micromolar inhibitor of α-N-acetylgalactosaminidases
    Best, Daniel
    Chairatana, Phoom
    Glawar, Andreas F. G.
    Crabtree, Elizabeth
    Butters, Terry D.
    Wilson, Francis X.
    Yu, Chu-Yi
    Wang, Wu-Bao
    Jia, Yue-Mei
    Adachi, Isao
    Kato, Atsushi
    Fleet, George W. J.
    [J]. TETRAHEDRON LETTERS, 2010, 51 (17) : 2222 - 2224
  • [10] Synthesis of 1,2-trans-2-Acetamido-2-deoxyhomoiminosugars
    Bleriot, Yves
    Anh Tuan Tran
    Prencipe, Giuseppe
    Jagadeesh, Yerri
    Auberger, Nicolas
    Zhu, Sha
    Gauthier, Charles
    Zhang, Yongmin
    Desire, Jerome
    Adachi, Isao
    Kato, Atsushi
    Sollogoub, Matthieu
    [J]. ORGANIC LETTERS, 2014, 16 (21) : 5516 - 5519
1234567