Synthesis and Biological Activity of Aminoacyl Analogs of Ascamycin(Organic Chemistry)
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概要
- 論文の詳細を見る
L-Prolyl and other aminoacyl derivatives of ascamycin (1) were synthesized by a condensation reaction of N^6-t-butyloxycarbonyl-2-chloro-9-(2', 3'-O-isopropylidene-5'-O-sulfamoyl-β-D-ribofuranosyl)adenine (9) with the corresponding t-butyloxycarbonylaminoacylimidazole in the presence of Cs_2CO_3 in DMF as the key step. The L-prolyl derivative (2) and L-phenylalanyl derivative (3) as well as 1 showed selective toxicity against Xanthomonas citri. The L-prolyl-L-prolyl derivative (5) as well as dealanylascamycin (6) showed broad toxicity against various Gram-negative and Gram-positive bacteria. The D-alanyl derivative (4) lost its antibacterial activity. 2 was the best substrate (15.3M/min per mg of protein) for an Xc-aminopeptidase (an ascamycin-dealanylating enzyme from X. citri cells) among these analogs. This enzyme scarcely hydrolyzed 4 (0.2 M/min per mg of protein). The substrate specificity of the enzyme accounts for antibacterial activity of the analogs. 2 showed greater selective toxicity against Kirsten sarcoma virus transformed Balb3T3 (KN-3T3) cells than against nontransformed cells (Balb 3T3).
- 社団法人日本農芸化学会の論文
- 1988-05-23
著者
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OSADA Hiroyuki
Antibiotics Laboratory, Discovery Research institute, RIKEN
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Magae J
Tokyo Inst. Technol. Yokohama Jpn
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Magae J
Inst. Res. And Innovation Kashiwa Jpn
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Isono K
Inst. Physical And Chemical Res. Saitama Jpn
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Uramoto M
Riken (the Institute Of Physical And Chemical Research)
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Uramoto M
Tamagawa Univ. Tokyo Jpn
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Uramoto M
Department Of Applied Biological Chemistry Tamagawa University
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Osada H
Antibiotics Laboratory Advanced Science Institute Riken
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Ueki Masashi
Riken Institute
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ISONO Kiyoshi
The Institute of Physical and Chemical Research, RIKEN
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ISONO Kiyoshi
Antibiotics Laboratory, RIKEN (The Institute of Physical and Chemical Research)
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UBUKATA Makoto
Antibiotics Laboratory, RIKEN, The Institute of Physical and Chemical Research
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MAGAE Junji
Antibiotics Laboratory, RIKEN, The Institute of Physical and Chemical Research
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URAMOTO Masakazu
The Institute of Physical and Chemical Research
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Isono K
The Institute Of Physical And Chemical Research Riken
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Isono Kiyoshi
Antibiotics Laboratory Riken (the Institute Of Physical And Chemical Research)
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Isono Kiyoshi
The Institute Of Physical And Chemical Research(riken)
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Isono Kiyoshi
The Institute Of Physical And Chemical Research (riken):(present Address) Department Of Marine Scien
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Osada Hiroyuki
Antibiotic Laboratory Riken (institute Of Physical And Chemical Research)
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Ubukata Makoto
Antibiotics Laboratory Riken (the Institute Of Physical And Chemical Research)
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Isono K
Tokai Univ. Shimizu Jpn
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