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Sigma-Aldrich

Sulfo-LC-SDA (Sulfo-NHS-LC-Diazirine) (sulfosuccinimidyl 6-(4,4′-azipentanamido)hexanoate)

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Empirical Formula (Hill Notation):
C15H21N4NaO8S
Molecular Weight:
440.40
MDL number:
MFCD28899432
UNSPSC Code:
12352200
PubChem Substance ID:
329768799
NACRES:
NA.22

Assay

≥90%

Quality Level

100

form

powder

mol wt

440.4

reaction suitability

reagent type: cross-linking reagent

storage condition

desiccated

solubility

water: soluble

shipped in

ambient

storage temp.

2-8°C

SMILES string

O=C(N1OC(CCCCCNC(CCC2(N=N2)C)=O)=O)CC(S(=O)([O-])=O)C1=O.[Na+]

InChI

1S/C15H22N4O8S.Na/c1-15(17-18-15)7-6-11(20)16-8-4-2-3-5-13(22)27-19-12(21)9-10(14(19)23)28(24,25)26;/h10H,2-9H2,1H3,(H,16,20)(H,24,25,26);/q;+1/p-1

InChI key

NZJSKWCJBUEDEO-UHFFFAOYSA-M

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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

  • Water soluble—solubility in aqueous solutions improved by a sulfonate group
  • 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.

related product

Product No.
Description
Pricing

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Photoactivatable crosslinking sugars for capturing glycoprotein interactions.
Yoshihito Tanaka et al.
Journal of the American Chemical Society, 130(11), 3278-3279 (2008-02-26)
Monika Suchanek et al.
Nature methods, 2(4), 261-267 (2005-03-23)
Protein-protein interactions are the key to organizing cellular processes in space and time. The only direct way to identify such interactions in their cellular environment is by photo-cross-linking. Here we present a new strategy for photo-cross-linking proteins in living cells.

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