Design and Synthesis of Peptide Mimetics of GDP-Fucose: Targeting Inhibitors of Fucosyltransferases

Synlett

Volumn , Issue 2, 2004, Pages 243-246

  Tanaka, Toru ^a   Tsuda, Chihiro ^a   Miura, Tsuyoshi ^b   Inazu, Toshiyuki ^b   Tsuji, Shuichi ^c   Nishihara, Shoko ^d   Hisamatsu, Mitsuko ^d   Kajimoto, Tetsuya ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

^b NOGUCHI INSTITUTE   (Japan)

^c OCHANOMIZU UNIVERSITY   (Japan)

^d SOKA UNIVERSITY   (Japan)

Author keywords

Aldol reactions; Amino acids; Enzymes; Inhibitors; Nucleotides

Indexed keywords

AMINO ACID; BETA HYDROXY ALPHA AMINO ACID; FRUCTOSE BISPHOSPHATE ALDOLASE; FUCOSE; GUANOSINE DIPHOSPHATE; NIKKOMYCIN Z; OLIGOSACCHARIDE; PEPTIDE DERIVATIVE; THREONINE; TRANSFERASE INHIBITOR; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CATALYSIS; CATALYST; DRUG ACTIVITY; DRUG DESIGN; DRUG POTENCY; DRUG SYNTHESIS; DRUG TARGETING; ENZYME INHIBITION;

EID: 1242296148     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-44984     Document Type: Article

References (27)

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17. 3): δ = 15.8, 20.6 x 2, 20.7, 28.4, 30.0, 64.2, 67.5, 68.0, 68.2, 71.1, 96.0, 115.0, 137.7, 170.0, 170.4, 170.6.
18. 3): δ = 1.23 (d, 3 H, J = 6.5 Hz, Me-6), 1.70 (m, 2 H), 2.00, 2.06, 2.18 (s, each 3 H, 3 x Ac), 2.11 (m, 2 H), 3.49 (m, 1 H), 3.81 (br q, 1 H, J = 6.5 Hz, H-5), 3.92 (dt, 1 H, J = 9.5, 6.0 Hz), 4.43 (d, 1 H, J = 7.5, H-1), 4.95-5.05 (m, 2 H), 5.02 (dd, 1 H, J = 3.0, 10.5 Hz, H-3), 5.20 (dd, 1 H, J = 7.0, 10.5 Hz, H-2), 5.24 (br d, 1 H, J = 3.0 Hz, H-4), 5.80 (ddt, 1 H, J = 10.0, 17.0, 6.5 Hz).
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23. 13: 716.3. Found: 717.4.
24. +: 523.2. Found: 523.1.
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27. 2O. After centrifugation of the reaction mixture, in order to detect the fucosylated products and estimate their amounts, each supernatant was filtered and subjected to reverse-phase HPLC analysis on TSK-gel ODS-80Ts QA column (4.6 x 250 mm; Tosoh, Tokyo, Japan) and eluted with 20 mM ammonium acetate buffer (pH 4.0) containing 7% MeOH at flow rate of 1.0 mL/min at 50°C, with monitoring by a fluorescence spectrophotometer (JASCO FP-920; Nihon Bunkoh, Tokyo, Japan).