One-pot synthesis of unsymmetrical disulfides using 1-chlorobenzotriazole as oxidant: Interception of the sulfenyl chloride intermediate
作者:Nashia Stellenboom、Roger Hunter、Mino R. Caira
DOI:10.1016/j.tet.2010.02.077
日期:2010.4
is described for unsymmetricaldisulfide synthesis from two different thiols using 1-chlorobenzotriazole (BtCl) as oxidant. The mechanism of the coupling involves in situ trapping of the sulfenyl chloride intermediate R1SCl by nucleophilic benzotriazole (BtH) to form R1SBt, which protects R1SCl from forming the homodimer R1SSR1. The methodology is applicable to all types of thiol (aliphatic, aromatic
描述了一种高产,低温的一锅法,用于使用1-氯苯并三唑(BtCl)作为氧化剂由两种不同的硫醇合成不对称的二硫键。偶联的机制包括通过亲核苯并三唑(BtH)原位捕获亚磺酰氯中间体R 1 SCl形成R 1 SBt,从而保护R 1 SCl避免形成同型二聚体R 1 SSR 1。该方法适用于所有类型的硫醇(脂族,芳族,杂芳族),并为脂族-脂族偶联开发了一种变体。差异性的N-保护的半胱氨酸偶合,以高收率(90%)提供不对称的胱氨酸衍生物,该模型可作为含半胱氨酸的肽单分子间偶联形成肽二硫键异二聚体的模型。由于条件温和,因此注意到芳香族-芳香族二硫化物合成中的交换最少。
POLYNUCLEOTIDE CONSTRUCTS HAVING DISULFIDE GROUPS
申请人:BRADSHAW Curt W.
公开号:US20160257961A1
公开(公告)日:2016-09-08
The invention features polynucleotide constructs containing one or more components (i) containing a disulfide linkage, where each of the one or more components is attached to an internucleotide bridging group or a terminal group of the polynucleotide construct, and each of the one or more components (i) contains one or more bulky groups proximal to the disulfide group. The invention also features polynucleotide constructs containing one or more components (i) containing a disulfide linkage, where each of the one or more components (i) is attached to an internucleotide bridging group or a terminal group of the polynucleotide construct, and each of the one or more components (i) contains at least 4 atoms in a chain between the disulfide linkage and the phosphorus atom of the internucleotide bridging group or the terminal group; and where the chain does not contain a phosphate, an amide, an ester, or an alkenylene. The invention also features methods of delivering a polynucleotide to a cell using the polynucleotide constructs of the invention.
[EN] POLYNUCLEOTIDE CONSTRUCTS HAVING BIOREVERSIBLE AND NON-BIOREVERSIBLE GROUPS<br/>[FR] CONSTRUCTIONS DE POLYNUCLÉOTIDES POSSÉDANT DES GROUPES BIORÉVERSIBLES ET NON BIORÉVERSIBLES
申请人:SOLSTICE BIOLOG LTD
公开号:WO2015188197A3
公开(公告)日:2016-02-25
POLYNUCLEOTIDE CONSTRUCTS HAVING BIOREVERSIBLE AND NON-BIOREVERSIBLE GROUPS
申请人:BRADSHAW Curt W.
公开号:US20170114341A1
公开(公告)日:2017-04-27
The invention features a hybridized polynucleotide construct containing a passenger strand, a guide strand loadable into a RISC complex, and (i) a 3′-terminal or an internucleotide non-bioreversible group in the guide strand; or (ii) a 5′-terminal, a 3′-terminal, or an internucleotide non-bioreversible group in the passenger strand, and a 5′-terminal, a 3′-terminal, or an internucleotide disulfide bioreversible group in the guide strand or the passenger strand. The invention also features methods of delivering a polynucleotide to a cell using the hybridized polynucleotide construct. The invention further features methods of reducing the expression of a polypeptide in a cell using the hybridized polynucleotide construct.
[EN] POLYNUCLEOTIDE CONSTRUCTS HAVING DISULFIDE GROUPS<br/>[FR] CONSTRUCTIONS POLYNUCLÉOTIDIQUES CONTENANT DES GROUPES DISULFURE
申请人:SOLSTICE BIOLOG LTD
公开号:WO2015069932A1
公开(公告)日:2015-05-14
The invention features polynucleotide constructs containing one or more components (i) containing a disulfide linkage, where each of the one or more components is attached to an internudeotide bridging group or a terminal group of the polynucleotide construct, and each of the one or more components (i) contains one or more bulky groups proximal to the disulfide group. The invention also features polynucleotide constructs containing one or more components (i) containing a disulfide linkage, where each of the one or more components (i) is attached to an internudeotide bridging group or a terminal group of the polynucleotide construct, and each of the one or more components (i) contains at least 4 atoms in a chain between the disulfide linkage and the phosphorus atom of the internudeotide bridging group or the terminal group; and where the chain does not contain a phosphate, an amide, an ester, or an alkenylene. The invention also features methods of delivering a polynucleotide to a cell using the polynucleotide constructs of the invention.