Chemical modification of the GE 2270A macrocycle (MDL 62,879)

被引：10

作者：

Tavecchia, P ^{[1
]}

Kurz, M ^{[1
]}

Colombo, L ^{[1
]}

Bonfichi, R ^{[1
]}

Selva, E ^{[1
]}

Lociuro, S ^{[1
]}

Marzorati, E ^{[1
]}

Ciabatti, R ^{[1
]}

机构：

[1] HOECHST AG,CENT PHARMA RES,D-65926 FRANKFURT,GERMANY

来源：

TETRAHEDRON | 1996年 / 52卷 / 26期

关键词：

D O I：

10.1016/0040-4020(96)00417-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Controlled acid hydrolysis of compound 2 resulted in the selective opening of the macrocycle while in basic condition a retro-aldol reaction occurred at the level of phenylserine thiazole. Compound 2 can be easily prepared from the natural antibiotic MDL 62,879. All the compounds prepared resulted less active than MDL 62,879. Copyright (C) 1996 Elsevier Science Ltd

引用

收藏

页码：8763 / 8774

页数：12

相关论文

共 12 条

[1] NEW ANTIBIOTIC THAT ACTS SPECIFICALLY ON THE GTP-BOUND FORM OF ELONGATION FACTOR-TU [J].

ANBORGH, PH ;

PARMEGGIANI, A .

EMBO JOURNAL, 1991, 10 (04) :779-784

[2]

BERDY J, 1980, HDB ANTIBIOTICS COMP

[3]

BUSH KL, 1988, MASS SPECTROMETRY MA, P82

[4] INHIBITION OF BACTERIAL PROTEIN-SYNTHESIS BY ELONGATION-FACTOR-TO-BINDING ANTIBIOTICS MDL-62,879 AND EFROTOMYCIN [J].

LANDINI, P ;

BANDERA, M ;

GOLDSTEIN, BP ;

RIPAMONTI, F ;

SOFFIENTINI, A ;

ISLAM, K ;

DENARO, M .

BIOCHEMICAL JOURNAL, 1992, 283 :649-652

[5] MECHANISM OF ACTION OF KIRROMYCIN-LIKE ANTIBIOTICS [J].

PARMEGGIANI, A ;

SWART, GWM .

ANNUAL REVIEW OF MICROBIOLOGY, 1985, 39 :557-577

[6] ANTIBIOTIC GE2270-A - A NOVEL INHIBITOR OF BACTERIAL PROTEIN-SYNTHESIS .1. ISOLATION AND CHARACTERIZATION [J].

SELVA, E ;

BERETTA, G ;

MONTANINI, N ;

SADDLER, GS ;

GASTALDO, L ;

FERRARI, P ;

LORENZETTI, R ;

LANDINI, P ;

RIPAMONTI, F ;

GOLDSTEIN, BP ;

BERTI, M ;

MONTANARO, L ;

DENARO, M .

JOURNAL OF ANTIBIOTICS, 1991, 44 (07) :693-701

[7] NOVEL ANTIBIOTICS, AMYTHIAMICINS .4. A MUTATION IN THE ELONGATION-FACTOR TU GENE IN A RESISTANT MUTANT OF BACILLUS-SUBTILIS [J].

SHIMANAKA, K ;

IINUMA, H ;

HAMADA, M ;

IKENO, S ;

TSUCHIYA, KS ;

ARITA, M ;

HORI, M .

JOURNAL OF ANTIBIOTICS, 1995, 48 (02) :182-184

[8] STRUCTURE REVISION OF THE ANTIBIOTIC PULVOMYCIN [J].

SMITH, RJ ;

WILLIAMS, DH ;

BARNA, JCJ ;

MCDERMOTT, IR ;

HAEGELE, KD ;

PIRIOU, F ;

WAGNER, J ;

HIGGINS, W .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (10) :2849-2857

[9] ANTIBIOTIC GE37468-A - A NEW INHIBITOR OF BACTERIAL PROTEIN-SYNTHESIS .1. ISOLATION AND CHARACTERIZATION [J].

STELLA, S ;

MONTANINI, N ;

LEMONNIER, F ;

FERRARI, P ;

COLOMBO, L ;

MARINELLI, F ;

LANDINI, P ;

CICILIATO, I ;

GOLDSTEIN, BP ;

SELVA, E ;

DENARO, M .

JOURNAL OF ANTIBIOTICS, 1995, 48 (08) :780-786

[10] RAPID CHROMATOGRAPHIC TECHNIQUE FOR PREPARATIVE SEPARATIONS WITH MODERATE RESOLUTION [J].

STILL, WC ;

KAHN, M ;

MITRA, A .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (14) :2923-2925