Disuccinimidyl suberate

Base Information

• Chemical Name: Disuccinimidyl suberate
• CAS No.: 68528-80-3
• Molecular Formula: C16H20N2O8
• Molecular Weight: 368.343
• Hs Code.: 29171900
• European Community (EC) Number: 271-216-2,614-576-1
• NSC Number: 340008
• DSSTox Substance ID: DTXSID70988200
• Nikkaji Number: J277.742H
• Wikipedia: Disuccinimidyl_suberate
• Wikidata: Q3885907
• Mol file: 68528-80-3.mol

Synonyms:1,1'-((1,8-dioxo-1,8-octanediyl)bis(oxy))bis-2,5-pyrrolidinedione;DSIS;N-hydroxysuccinimide suberic acid ester;NHS-SA

Chemical Property of Disuccinimidyl suberate

Chemical Property:

• Melting Point: 169-170 °C
• Boiling Point: 513.5 °C at 760 mmHg
• Flash Point: 264.4 °C
• PSA: 127.36000
• Density: 1.4 g/cm³
• LogP: 0.41720
• Storage Temp.: 2-8°C
• Solubility.: chloroform: 50 mg/mL
• Water Solubility.: Insoluble in water. Soluble in chloroform: 50 mg/mL.
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 11
• Exact Mass: 368.12196560
• Heavy Atom Count: 26
• Complexity: 544

Purity/Quality:

98%,99%, ^*data from raw suppliers

Suberic acid bis(N-hydroxysuccinimide ester) ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: UVCB
• Canonical SMILES: C1CC(=O)N(C1=O)OC(=O)CCCCCCC(=O)ON2C(=O)CCC2=O
• Description: DSS Crosslinker is a membrane permeable, noncleavable crosslinker. The NHS ester groups are reactive toward primary amines.
• Uses: Suberic acid bis(N-hydroxysuccinimide ester) has been:supplemented in pierce lysis buffer used for immunoprecipitationused to conjugate the oligonucleotide standards to gelatinused in cross-linking of ASC (apoptosis-associated speck-like protein containing a caspase recruitment domain) oligomers Disuccinimidyl suberate (DSS) is a bifunctional cross-linking reagent which contains two N-hydroxysuccinimide esters that are reactive toward primary amines. DSS is membrane-permeable and is commonly used to cross-link proteins in intact cells. Disuccinimidyl suberate is a homobifunctional amine-reactive crosslinker. It is usually coupled to molecules containing primary amines via amide bonds buffered at pH 7.5 (6.5-8.5). It incorporates an 8-atom spacer arm.

Technology Process of Disuccinimidyl suberate

There total 2 articles about Disuccinimidyl suberate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + octane-1,8-dioic acid (505-48-6) → disuccinimidyl suberate (68528-80-3)

Guidance literature:

With dicyclohexyl-carbodiimide; In tetrahydrofuran;

DOI:10.1039/b613469f

Reference yield:

→ disuccinimidyl suberate (68528-80-3)

Guidance literature:

Reference yield: 100.0%

S-trityl-L-cysteine (2799-07-7) + disuccinimidyl suberate (68528-80-3) → (R)-2-(8-(((R)-1-carboxy-2-(tritylthio)ethyl)amino)-8-oxooctanamido)-3-(tritylthio)propanoic acid (1446417-16-8)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1055/s-0032-1318407

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

octane-1,8-dioic acid

Downstream raw materials:

2-(benzyloxycarbonylamino)-6-(7-carboxyheptanoylamino)hexanoic acid

2-(benzyloxycarbonylamino)-6-(7-(5-(benzyloxycarbonylamino)-5-carboxypentylaminocarbonyl)heptanoylamino)hexanoic acid

2-{3-[5-[7-(2,5-dioxopyrrolidin-1-yloxycarbonyl)heptanoylamino]-1-(4-methoxybenzyloxycarbonyl)pentyl]ureido}pentanedioic acid bis-(4-methoxybenzyl) ester

C₈₄H₁₂₇N₁₇O₂₈S

Refernces

• 1、 -. "DLL3-TARGETING MULTISPECIFIC ANTIGEN-BINDING MOLECULES AND USES THEREOF". . . Retrieved 2021/10/02.
• 2、 -. "SITE SELECTIVE CONJUGATION OF AN OLIGONUCLEOTIDE CONJUGATE OR A SMALL MOLECULE TO A METAL BINDING PROTEIN". Page/Page column 42. . Retrieved 2016/01/25.