803413

SDA (NHS-Diazirine) (succinimidyl 4,4′-azipentanoate)

• Synonym(s): 2,5-Dioxo-1-pyrrolidinyl 3-methyl-3H-diazirine-3-propanoate, NHS-diazirine Succinimidyl 4,4′-azipentanoate, SDA, Succinimidyl-diazirine
• Empirical Formula (Hill Notation): C₉H₁₁N₃O₄
• Molecular Weight: 225.20
• MDL number: MFCD28899672
• UNSPSC Code: 12352200
• PubChem Substance ID: 329768804
• NACRES: NA.22

Properties

• Assay: ≥90%
• Quality Level: 100
• form: powder
• mol wt: 225.2
• reaction suitability: reagent type: cross-linking reagent
• storage condition: desiccated
• solubility: DMSO or DMF: soluble
• shipped in: ambient
• storage temp.: 2-8°C
• SMILES string: CC1(N=N1)CCC(ON2C(CCC2=O)=O)=O
• InChI: 1S/C9H11N3O4/c1-9(10-11-9)5-4-8(15)16-12-6(13)2-3-7(12)14/h2-5H2,1H3
• InChI key: SYYLQNPWAPHRFV-UHFFFAOYSA-N

Description

General description

Succinimidyl-diazirine (SDA) reagents are a new class of crosslinkers that combine proven amine-reactive chemistry with an innovative and efficient diazirine-based photochemistry for conjugating amine-containing molecules to nearly any other functional group. The SDA crosslinkers include six compounds differing in spacer arm lengths, ability to cleave the crosslinked proteins, and presence or absence of a charged group for membrane permeability. Protein crosslinking is an important technique used to understand protein structure and to stabilize protein-protein interactions, and these SDA reagents extend the efficiency and range of interactions that can be explored by this approach.

Features and Benefits

• Membrane-permeable—suitable for in vivo intracellular protein crosslinking
• Heterobifunctional—NHS ester group reacts with primary amines at pH 7 to 9 to form covalent amide bonds; diazirine (azipentanoate) group reacts efficiently with any amino acid side chain or peptide backbone upon activation with long-wave UV light (330-370 nm)
• Controllable—two-step chemical crosslinking is activated using common laboratory UV lamps
• Easy to use—these crosslinkers are photo-stable under typical laboratory lighting conditions so there is no need to perform experiments in the dark
• Better than aryl azides—the diazirine photoreactive group has better photostability in normal light than phenyl azide groups of traditional photoreactive crosslinkers, yet the diazirine group is more efficiently activated by long-wave UV light

Caution

This product is sensitive to moisture. The vial is packaged in a resealable bag with a desiccant to reduce exposure to moisture. After cold storage, equilibrate the vial to room temperature before opening to reduce condensation inside the vial. Make fresh solutions. Storage of stock solutions is not recommended. After use, return the vial to the resealable bag. Close the bag and store the product at the recommended temperature.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable