Synthesis of (3R)-Amino-(2S)-Hydroxy Amino Acids for Inhibition of Methionine Aminopeptidase-1

References

• Suda , H. , Takita , T. , Aoyagi , T. and Umezawa , H. 1976 . J. Antibiot. , 29 : 100 – 102 .
   PubMed Web of Science ®Google Scholar
• Umezawa , Aoyagi , H. T. , Suda , H. , Hamada , M. and Takeuchi , T. 1976 . J. Antibiot. , 29 : 97 – 99 .
   PubMed Web of Science ®Google Scholar
• Aoyagi , T. , Hobe , H. , Kojima , F. , Hamada , M. , Takeuchi , T. and Umezawa , H. 1978 . J. Antibiot. , 31 : 636
   PubMed Web of Science ®Google Scholar
• Umezawa , H. 1978 . Antibiot Chemother. (Basel) , 24 : 9
   PubMedGoogle Scholar
• Ocain , T. D. and Rich , D. H. 1988 . J. Med. Chem. , 31 : 2193 – 2199 .
   PubMed Web of Science ®Google Scholar
• Rich , D. H. , Moon , B. J. and Harbeson , S. 1984 . J. Med. Chem. , 27 : 417 – 422 .
   PubMed Web of Science ®Google Scholar
• Gordon , E. M. , Godfrey , J. D. , Delaney , N. G. , Asaad , M. M. , Von Langen , D. and Cushman , D. W. 1988 . J. Med. Chem. , 31 : 2199 – 2211 .
   PubMed Web of Science ®Google Scholar
• Flinta , C. , Persson , B. , Jornvall , H. and von Heijne , G. 1986 . Eur. J. Biochem. , 154 : 193 – 196 .
   PubMedGoogle Scholar
• Li , G. , Angert , H. H. and Sharpless , K. B. 1996 . Angew. Chem. Int. Ed. Engl. , 35 : 2913 – 2817 .
   Google Scholar
• Li , G. , Chang , H. and Sharpless , K. B. 1996 . Angew. Chem. Int. Ed. Engl. , 35 : 451 – 453 .
   Web of Science ®Google Scholar
• Burley , S. K. , David , P. R. and Lipscomb , W. N. 1991 . Proc. Natl. Acad. Sci. USA , 88 : 6916 – 6920 .
   PubMed Web of Science ®Google Scholar
• Takita , T. , Nishizawa , R. , Saino , T. , Suda , H. , Aoyagi , T. and Umezawa , H. 1977 . J. Med. Chem. , 20 : 510
   PubMedGoogle Scholar
• Lim , S. 1994 . Ph.D. Thesis University of Wisconsin at Madison .
   Google Scholar
• Ben-Bassat , A. , Bauer , K. , Chang , S. , Myambo , K. , Boosman , A. and Chang , S. 1987 . J. Bacteriol. , 169 : 751 – 757 . Inhibition of E. coli MetAP-1 by compounds 1—3 was measured by an assay similar to that developed by Ben-Bassat (4 mM substrate at pH 7.4; room temperature or 30°; 30 min. preincubation). Compounds 1—3 had IC50 values of 5—7 μM
   PubMed Web of Science ®Google Scholar
• Rich , D. H. , Moon , B. J. and Boparai , A. 1980 . J. Org. Chem. , 45 : 2288 – 2290 .
   Google Scholar
• Recrystallization of 6 from methanol afforded 85 %ee; mp 73—73.5°C (uncorrected); [a]23 D=+62.6 (c=1.0 MeOH)
   Google Scholar