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
  • [11] 2'-AZIDO-2'-DEOXY- AND 2'-AMINO-2'-DEOXY-BETA-D-ARABINO-FURANOSYL PURINE NUCLEOSIDES
    BOBEK, M
    [J]. CARBOHYDRATE RESEARCH, 1979, 70 (02) : 263 - 273
  • [12] Amidation of esters assisted by Mg(OCH3)2 or CaCl2
    Bundesmann, Mark W.
    Coffey, Steven B.
    Wright, Stephen W.
    [J]. TETRAHEDRON LETTERS, 2010, 51 (30) : 3879 - 3882
  • [13] Asymmetric synthesis of α,β-diamino acid derivatives with an aziridine-, azetidine- and γ-lactone-skeleton via Mannich-type additions across α-chloro-N-sulfinylimines
    Callebaut, Gert
    Mangelinckx, Sven
    Kiss, Lorand
    Sillanpaa, Reijo
    Fueloep, Ferenc
    De Kimpe, Norbert
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (11) : 2326 - 2338
  • [14] Synthesis of the enantiomers of XYLNAc and LYXNAc: comparison of β-N-acetylhexosaminidase inhibition by the 8 stereoisomers of 2-N-acetylamino-1,2,4-trideoxy-1,4-iminopentitols
    Crabtree, Elizabeth V.
    Martinez, R. Fernando
    Nakagawa, Shinpei
    Adachi, Isao
    Butters, Terry D.
    Kato, Atsushi
    Fleet, George W. J.
    Glawar, Andreas F. G.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (23) : 3932 - 3943
  • [15] Stereoselective synthesis of 2-acetamido-1,2-dideoxynojirimycin (DNJNAc) and ureido-DNJNAc derivatives as new hexosaminidase inhibitors
    De la Fuente, Alex
    Mena-Barragan, Teresa
    Farrar-Tobar, Ronald A.
    Verdaguer, Xavier
    Garcia Fernandez, Jose M.
    Ortiz Mellet, Carmen
    Riera, Antoni
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (23) : 6500 - 6510
  • [16] SYNTHESIS OF 2-ACETAMIDO-1,5-IMINO-1,2,5-TRIDEOXY-D-MANNITOL AND OF 2-ACETAMIDO-1,5-IMINO-1,2,5-TRIDEOXY-D-GLUCITOL, A POTENT AND SPECIFIC INHIBITOR OF A NUMBER OF BETA-N-ACETYLGLUCOSAMINIDASES
    FLEET, GWJ
    SMITH, PW
    NASH, RJ
    FELLOWS, LE
    PAREKH, RB
    RADEMACHER, TW
    [J]. CHEMISTRY LETTERS, 1986, (07) : 1051 - 1054
  • [17] SYNTHESIS OF DEOXYMANNOJIRIMYCIN FAGOMINE DEOXYNOJIRIMYCIN 2-ACETAMIDO-1,5-IMINO-1,2,5-TRIDEOXY-D-MANNITOL 2-ACETAMIDO-1,5-IMINO-1,2,5-TRIDEOXY-D-GLUCITOL 2S, 3R, 4R, 5R-TRIHYDROXYPIPECOLIC ACID AND 2S, 3R, 4R, 5S-TRIHYDROXYPIPECOLIC ACID FROM METHYL 3-O-BENZYL-2,6-DIDEOXY-2,6-IMINO-ALPHA-D-MANNOFURANOSIDE
    FLEET, GWJ
    FELLOWS, LE
    SMITH, PW
    [J]. TETRAHEDRON, 1987, 43 (05) : 979 - 990
  • [18] A PRACTICAL SYNTHESIS OF DEOXYMANNOJIRIMYCIN AND OF (2S, 3R, 4R, 5R)-3,4,5-TRIHYDROXYPIPECOLIC ACID FROM D-GLUCOSE
    FLEET, GWJ
    RAMSDEN, NG
    WITTY, DR
    [J]. TETRAHEDRON, 1989, 45 (01) : 327 - 336
  • [19] AZETIDINE-2-CARBOXYLIC ACID - NEW CONSTITUENT OF PLANTS
    FOWDEN, L
    [J]. NATURE, 1955, 176 (4477) : 347 - 348
  • [20] Azetidine- and N-carboxylic azetidine-iminosugars as amyloglucosidase inhibitors: synthesis, glycosidase inhibitory activity and molecular docking studies
    Gavale, Kishor S.
    Chavan, Shrawan R.
    Khan, Ayesha
    Joshi, Rakesh
    Dhavale, Dilip D.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (23) : 6634 - 6646
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