A novel α,α ′ -diaminoacetic acid derivative for the introduction of the α-oxo aldehyde functionality into peptides
摘要:
A Fmoc-protected alpha,alpha'-diaminoacetic acid derivative acting as a masked glyoxylic acid equivalent was prepared in one step from glyoxylic acid and introduced into peptide chains after solid-phase peptide elongation. Deprotection and cleavage of the peptide from the solid support using trifluoroacetic acid was followed by unmasking of the glyoxylyl group in the presence of a base. This reagent allowed the synthesis of a glyoxylyl peptide using nonoxidizing conditions. (C) 2003 Elsevier Ltd. All rights reserved.
COMPOUNDS USEFUL IN PREPARING HYBRID IMMUNOGLOBULIN CONTAINING NON-PEPTIDYL LINKAGE
申请人:Capon, Daniel J.
公开号:EP3701971A1
公开(公告)日:2020-09-02
The present invention provides intermediate compounds containing a triazine or trans-cyclooctene group, useful in the preparation of compounds having the structure:
A-B-----Z
wherein A is a biologically active structure of the compound; wherein Z is a protein component of the compound, which protein component comprises one or more polypeptides, wherein at least one of the one or more polypeptides comprises consecutive amino acids which (i) are identical to a stretch of consecutive amino acids present in a chain of an Fc domain of an antibody; (ii) bind to an Fc receptor; and (iii) have at their N-terminus a sequence selected from the group consisting of a cysteine or selenocysteine; wherein the dashed line between B and Z represents a peptidyl linkage; and wherein the solid line between A and B represents a nonpeptidyl linkage.
本发明提供了含有三嗪或反式环辛烯基团的中间体化合物,可用于制备具有以下结构的化合物:
A-B-----Z
其中,A 是化合物的生物活性结构;Z 是化合物的蛋白质成分,该蛋白质成分包括一个或多个多肽,其中一个或多个多肽中至少有一个多肽包括连续氨基酸,这些连续氨基酸(i) 与抗体 Fc 结构域链中存在的一段连续氨基酸相同;(ii)与 Fc 受体结合;以及(iii)在其 N 端具有选自半胱氨酸或硒半胱氨酸组成的组的序列;其中 B 和 Z 之间的虚线代表肽基连接;而 A 和 B 之间的实线代表非肽基连接。
The present invention provides a compound having the structure:
A-B - - - Z
wherein A is a biologically active structure of the compound; wherein Z is a protein component of the compound, which protein component comprises one or more polypeptides, wherein at least one of the one or more polypeptides comprises consecutive amino acids which (i) are identical to a stretch of consecutive amino acids present in a chain of an Fc domain of an antibody; (ii) bind to an Fc receptor; and (iii) have at their N-terminus a sequence selected from the group consisting of a cysteine or selenocysteine; wherein the dashed line between B and Z represents a peptidyl linkage; and wherein the solid line between A and B represents a nonpeptidyl linkage, as well as intermediates dimers thereof, and processes of producing the compounds of the invention.
本发明提供了一种具有以下结构的化合物:
A-B - - Z
其中 A 是该化合物的生物活性结构;其中 Z 是该化合物的蛋白质组分,该蛋白质组分包括一个或多个多肽,其中一个或多个多肽中的至少一个多肽包括连续氨基酸,这些连续氨基酸(i) 与抗体的 Fc 结构域链中存在的一段连续氨基酸相同;(ii)与 Fc 受体结合;(iii)在其 N 端具有选自由半胱氨酸或硒半胱氨酸组成的组的序列;其中 B 和 Z 之间的虚线表示肽基连接;A 和 B 之间的实线表示非肽基连接,以及其中间体二聚体,以及生产本发明化合物的工艺。
The present invention provides a compound having the structure:
A-B-Z
wherein A is a biologically active structure of the compound; wherein Z is a protein component of the compound, which protein component comprises one or more polypeptides, wherein at least one of the one or more polypeptides comprises consecutive amino acids which (i) are identical to a stretch of consecutive amino acids present in a chain of an F
c
domain of an antibody; (ii) bind to an F
c
receptor; and (iii) have at their N-terminus a sequence selected from the group consisting of a cysteine or selenocysteine; wherein the dashed line between B and Z represents a peptidyl linkage; and wherein the solid line between A and B represents a nonpeptidyl linkage, as well as intermediates dimers thereof, and processes of producing the compounds of the invention.
A novel α,α ′ -diaminoacetic acid derivative for the introduction of the α-oxo aldehyde functionality into peptides
作者:Samia Far、Oleg Melnyk
DOI:10.1016/j.tetlet.2003.11.117
日期:2004.2
A Fmoc-protected alpha,alpha'-diaminoacetic acid derivative acting as a masked glyoxylic acid equivalent was prepared in one step from glyoxylic acid and introduced into peptide chains after solid-phase peptide elongation. Deprotection and cleavage of the peptide from the solid support using trifluoroacetic acid was followed by unmasking of the glyoxylyl group in the presence of a base. This reagent allowed the synthesis of a glyoxylyl peptide using nonoxidizing conditions. (C) 2003 Elsevier Ltd. All rights reserved.