A new strategy for solid-phase depsipeptide synthesis using recoverable building blocks

被引:22
作者
Albericio, F
Burger, K
Ruíz-Rodríguez, J
Spengler, J
机构
[1] Univ Barcelona, Barcelona Biomed Res Inst, E-08028 Barcelona, Spain
[2] Univ Leipzig, Dept Organ Chem, D-04103 Leipzig, Germany
关键词
D O I
10.1021/ol047653v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The technique of choice for synthesis of small-scale depsipeptides is on a solid support. However, if expensive monomers have to be incorporated, solid-phase synthesis can quickly turn out to be unattractive because of its low atom economy. Herein, we describe a new type of recoverable and reuseable alpha-hydroxy acid building block for solid-phase synthesis and its application in the synthesis of a number of small cyclic depsipeptides.
引用
收藏
页码:597 / 600
页数:4
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共 28 条
[1]   Structural analysis of peptide helices containing centrally positioned lactic acid residues [J].
Aravinda, S ;
Shamala, N ;
Das, C ;
Balaram, P .
BIOPOLYMERS, 2002, 64 (05) :255-267
[2]   Synthesis and biological evaluation of destruxin A and related analogs [J].
Ast, T ;
Barron, E ;
Kinne, L ;
Schmidt, M ;
Germeroth, L ;
Simmons, K ;
Wenschuh, H .
JOURNAL OF PEPTIDE RESEARCH, 2001, 58 (01) :1-11
[3]   Total synthesis of HUN-7293 [J].
Boger, DL ;
Keim, H ;
Oberhauser, B ;
Schreiner, EP ;
Foster, CA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (26) :6197-6205
[4]   From production of peptides in milligram amounts for research to multi-tons quantities for drugs of the future [J].
Bruckdorfer, T ;
Marder, O ;
Albericio, F .
CURRENT PHARMACEUTICAL BIOTECHNOLOGY, 2004, 5 (01) :29-43
[5]   Hexafluoroacetone as protection and activation reagent in amino acid and peptide chemistry.: Regiospecific α-functionalization of aspartic acid [J].
Burger, K ;
Lange, T ;
Rudolph, M .
HETEROCYCLES, 2003, 59 (01) :189-198
[6]   Solution-phase parallel synthesis of a pharmacophore library of HUN-7293 analogues: A general chemical mutagenesis approach to defining structure-function properties of naturally occurring cyclic (depsi)peptides [J].
Chen, Y ;
Bilban, M ;
Foster, CA ;
Boger, DL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (19) :5431-5440
[7]   Restricted conformation analogues of an anthelmintic cyclodepsipeptide [J].
Dutton, FE ;
Lee, BH ;
Johnson, SS ;
Coscarelli, EM ;
Lee, PH .
JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (11) :2057-2073
[8]   Stereochemical requirements for beta-hairpin formation: Model studies with four-residue peptides and depsipeptides [J].
Haque, TS ;
Little, JC ;
Gellman, SH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (29) :6975-6985
[9]   Syntheses of hapalosin analogs by solid-phase assembly of acyclic precursors [J].
Hermann, C ;
Giammasi, C ;
Geyer, A ;
Maier, ME .
TETRAHEDRON, 2001, 57 (43) :8999-9010
[10]   Total synthesis of (-)-tamandarin B [J].
Joullié, MM ;
Portonovo, P ;
Liang, B ;
Richard, DJ .
TETRAHEDRON LETTERS, 2000, 41 (49) :9373-9376