Synthesis of the liposidomycin diazepanone nucleoside

被引：36

作者：

Knapp, S ^{[1
]}

Morriello, GJ

Doss, GA

机构：

[1] Rutgers State Univ, Dept Chem & Biol Chem, Piscataway, NJ 08854 USA

[2] Merck & Co Inc, Rahway, NJ 07065 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 04期

关键词：

D O I：

10.1021/ol0102904

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The synthesis of the liposidomycin degradation product 4 from D-glucose establishes Its stereochemistry as 5'S,6'S and, by Incorporation of the earlier diazepanone relative stereochemical assignment, establishes the absolute stereochemistry of the liposidomycins 1 and 2 as 5'S,6'S,2"'S,3"'S.

引用

页码：603 / 606

页数：4

共 19 条

[1] REDUCTIVE AMINATION OF ALDEHYDES AND KETONES BY USING SODIUM TRIACETOXYBOROHYDRIDE [J].

ABDELMAGID, AF ;

MARYANOFF, CA ;

CARSON, KG .

TETRAHEDRON LETTERS, 1990, 31 (39) :5595-5598

[2] A NEW CONVENIENT REAGENT FOR PEPTIDE SYNTHESES [J].

BELLEAU, B ;

MALEK, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (06) :1651-&

[3] Modes of action of tunicamycin, liposidomycin B, and mureidomycin A: Inhibition of phospho-N-acetylmuramyl-pentapeptide translocase from Escherichia coli [J].

Brandish, PE ;

Kimura, K ;

Inukai, M ;

Southgate, R ;

Lonsdale, JT ;

Bugg, TDH .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1996, 40 (07) :1640-1644

[4] A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS [J].

CARLSEN, PHJ ;

KATSUKI, T ;

MARTIN, VS ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3936-3938

[5] New types of liposidomycins produced by Streptomyces that inhibit bacterial peptidoglycan synthesis -: Structure elucidation of fatty acid components by tandem mass spectrometry [J].

Esumi, Y ;

Suzuki, Y ;

Kimura, KI ;

Yoshihama, M ;

Ichikawa, T ;

Uramoto, M .

JOURNAL OF ANTIBIOTICS, 1999, 52 (03) :281-287

[6] LIPOSIDOMYCINS - NOVEL NUCLEOSIDE ANTIBIOTICS WHICH INHIBIT BACTERIAL PEPTIDOGLYCAN SYNTHESIS [J].

ISONO, K ;

URAMOTO, M ;

KUSAKABE, H ;

KIMURA, KI ;

IZAKI, K ;

NELSON, CC ;

MCCLOSKEY, JA .

JOURNAL OF ANTIBIOTICS, 1985, 38 (11) :1617-1621

[7]

Katsuki T., 1996, ORG REACT, V48, P1, DOI 10.1002/0471264180.or048.01

[8] LIPOSIDOMYCIN-C INHIBITS PHOSPHO-N-ACETYLMURAMYL-PENTAPEPTIDE TRANSFERASE IN PEPTIDOGLYCAN SYNTHESIS OF ESCHERICHIA-COLI Y-10 [J].

KIMURA, K ;

MIYATA, N ;

KAWANISHI, G ;

KAMIO, Y ;

IZAKI, K ;

ISONO, K .

AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1989, 53 (07) :1811-1815

[9] Assignment of the liposidomycin diazepanone stereochemistry [J].

Knapp, S ;

Morriello, GJ ;

Nandan, SR ;

Emge, TJ ;

Doss, GA ;

Mosley, RT ;

Chen, LJ .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (17) :5822-5831

[10] SYNTHESIS OF COMPLEX NUCLEOSIDE ANTIBIOTICS [J].

KNAPP, S .

CHEMICAL REVIEWS, 1995, 95 (06) :1859-1876

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