Title:
N-置換オリゴマーの合成
Document Type and Number:
Japanese Patent JP3596752
Kind Code:
B2
Abstract:
Poly N-substituted Glycines (poly NSGs), wherein the substituents bear purine or pyrimidine bases (R<9>) every second glycine: In addition, a solid phase method for the synthesis of N-substituted oligomers of more general structures is disclosed.The poly NSGs obtainable by this method can have a wide variety of side-chain substituents. Each N-substituted glycine monomer is assembled from two "sub-monomers" directly on the solid support. Each cycle of monomer addition consists of two steps: (1) acylation of a secondary amine bound to the support with an acylating agent comprising a leaving group capable of nucleophilic displacement by -NH2, such as a haloacetic acid, and (2) introduction of the side-chain by nucleophilic displacement of the leaving group, such as halogen (as a resin-bound alpha -haloacetamide) with a sufficient amount of a second sub-monomer comprising an -NH2 group, such as a primary amine, alkoxyamine, semicarbazide, acyl hydrazide, carbazate or the like. Repetition of the two step cycle of acylation and displacement gives the desired oligomers. The efficient synthesis of a wide variety of oligomeric NSGs using the automated synthesis technology of the present method makes these oligomers attractive candidates for the generation and rapid screening of diverse peptidomimetic libraries. The oligomers of the invention, such as N-substituted glycines (i.e. poly NSGs) disclosed here provide a new class of peptide-like compounds not found in nature, but which are synthetically accessible and have been shown to possess significant biological activity and proteolytic stability.
Inventors:
Ronald N. Zuckerman
Janice M. Kerr
Stephen Bryan Henry, Kent
Walter H. Moose
Reina Jay. Simon
Dane A. Goff
Janice M. Kerr
Stephen Bryan Henry, Kent
Walter H. Moose
Reina Jay. Simon
Dane A. Goff
Application Number:
JP2000038885A
Publication Date:
December 02, 2004
Filing Date:
February 16, 2000
Export Citation:
Assignee:
Chiron Corporation
International Classes:
A61K31/708; A61K31/785; A61K38/00; A61K38/16; A61K39/00; A61K39/395; A61K48/00; C07B43/06; C07C231/02; C07C237/22; C07C231/12; C07C237/42; C07K1/04; C07K1/08; C07K7/06; C07K7/08; C07K14/00; C08G69/08; C08G69/10; C07K; (IPC1-7): C07C231/12; A61K31/708; A61K31/785; A61K38/00; A61K39/00; A61K39/395; A61K48/00; C07C231/02; C07C237/22; C08G69/08
Domestic Patent References:
| JP8501565A |
Foreign References:
| WO1992013018A1 |
Other References:
泉屋信夫,他「ペプチド合成の基礎と実験」丸善(昭和60年)P.5-6、P.194-233
日本化学会編「新実験化学講座19高分子化学▲I▼」丸善(昭和53年)P.127-145
日本化学会編「新実験化学講座19高分子化学▲I▼」丸善(昭和53年)P.127-145
Attorney, Agent or Firm:
Hidesaku Yamamoto