N-Fmoc-aminooxy-2-chlorotrityl polystyrene resin: A facile solid-phase methodology for the synthesis of hydroxamic acids

被引:79
作者
Mellor, SL
McGuire, C
Chan, WC
机构
[1] Dept. of Pharmaceutical Sciences, University of Nottingham, University Park, Nottingham
关键词
D O I
10.1016/S0040-4039(97)00594-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Using the new compound N-Fmoc-hydroxylamine 1 we have generated a facile route to a high loading, acid labile solid-phase resin bearing a hydroxylamine linker. The novel N-Fmoc-aminooxy-2-chlorotrityl polystyrene 2 showed generic utility for the construction of hydroxamic acids, including peptidyl hydroxamic acids. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:3311 / 3314
页数:4
相关论文
共 12 条
[1]  
BARLOS K, 1991, INT J PEPT PROT RES, V37, P513
[2]   HYDROXAMIC ACIDS AS POTENT INHIBITORS OF ENDOTHELIN-CONVERTING ENZYME FROM HUMAN BRONCHIOLAR SMOOTH-MUSCLE [J].
BIHOVSKY, R ;
LEVINSON, BL ;
LOEWI, RC ;
ERHARDT, PW ;
POLOKOFF, MA .
JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (12) :2119-2129
[3]   HYDROXYLATED AROMATIC INHIBITORS OF HIV-1 INTEGRASE [J].
BURKE, TR ;
FESEN, MR ;
MAZUMDER, A ;
WANG, J ;
CAROTHERS, AM ;
GRUNBERGER, D ;
DRISCOLL, J ;
KOHN, K ;
POMMIER, Y .
JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (21) :4171-4178
[4]   SYNTHESIS OF THE SPIDER TOXINS NEPHILATOXIN-9 AND NEPHILATOXIN-11 BY A NOVEL SOLID-PHASE STRATEGY [J].
BYCROFT, BW ;
CHAN, WC ;
HONE, ND ;
MILLINGTON, S ;
NASH, IA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (16) :7415-7416
[5]   A NOVEL LYSINE-PROTECTING PROCEDURE FOR CONTINUOUS-FLOW SOLID-PHASE SYNTHESIS OF BRANCHED PEPTIDES [J].
BYCROFT, BW ;
CHAN, WC ;
CHHABRA, SR ;
HONE, ND .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (09) :778-779
[6]   ADVANTAGEOUS APPLICATIONS OF AZABENZOTRIAZOLE (TRIAZOLOPYRIDINE)-BASED COUPLING REAGENTS TO SOLID-PHASE PEPTIDE-SYNTHESIS [J].
CARPINO, LA ;
EL-FAHAM, A ;
MINOR, CA ;
ALBERICIO, F .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (02) :201-203
[7]   1-HYDROXY-7-AZABENZOTRIAZOLE - AN EFFICIENT PEPTIDE COUPLING ADDITIVE [J].
CARPINO, LA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) :4397-4398
[8]   A method for the synthesis of hydroxamic acids on solid phase [J].
Floyd, CD ;
Lewis, CN ;
Patel, SR ;
Whittaker, M .
TETRAHEDRON LETTERS, 1996, 37 (44) :8045-8048
[9]   Dde - A selective primary amine protecting group: A facile solid phase synthetic approach to polyamine conjugates [J].
Nash, IA ;
Bycroft, BW ;
Chan, WC .
TETRAHEDRON LETTERS, 1996, 37 (15) :2625-2628
[10]   Antibacterial agents that inhibit lipid A biosynthesis [J].
Onishi, HR ;
Pelak, BA ;
Gerckens, LS ;
Silver, LL ;
Kahan, FM ;
Chen, MH ;
Patchett, AA ;
Galloway, SM ;
Hyland, SA ;
Anderson, MS ;
Raetz, CRH .
SCIENCE, 1996, 274 (5289) :980-982