803650

SBAP (succinimidyl 3-(bromoacetamido)propionate)

• Empirical Formula (Hill Notation): C₉H₁₁N₂O₅Br
• CAS Number: 57159-62-3
• Molecular Weight: 307.10
• MDL number: MFCD01863457
• UNSPSC Code: 12352106
• PubChem Substance ID: 329768824
• NACRES: NA.22

Properties

• assay: ≥90%
• Quality Level: 100
• form: powder
• mol wt: 307.1
• reaction suitability: reagent type: cross-linking reagent
• storage condition: desiccated
• solubility: DMSO or DMF: soluble
• functional group: NHS ester; bromo
• shipped in: ambient
• storage temp.: 2-8°C
• SMILES string: O=C(CCC1=O)N1OC(CCNC(CBr)=O)=O
• InChI: 1S/C9H11BrN2O5/c10-5-6(13)11-4-3-9(16)17-12-7(14)1-2-8(12)15/h1-5H2,(H,11,13)
• InChI key: WGMMKWFUXPMTRW-UHFFFAOYSA-N

Description

General description

SBAP is a sulfhydryl-reactive and amine-reactive heterobifunctional crosslinker. The reagent′s NHS ester reacts with primary amines at pH 7-9 to form stable amide bonds, and the bromacetyl reacts with sulfhydryl groups at pH >7.5 to form stable thioether bonds This reagent is useful for preparing cyclic peptides and peptide conjugates because the spacer maintains peptide-like character in the crosslinked species.

Features and Benefits

• Reactive groups: NHS ester and bromoacetyl
• Reactive toward: amino and sulfhydryl groups
• NHS ester reacts with primary amines at pH 7-9 to form a stable amide bond
• Bromacetyl group reacts with sulfhydryl groups at pH > 7.5 to form stable thioether bonds
• Non-cleavable
• Water-insoluble (dissolve first in DMF or DMSO)
• Spacer maintains peptide-like character in the crosslinked species
• Resulting crosslink is susceptible to acid hydrolysis
• Useful for preparing cyclic peptides and peptide conjugates

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

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319,H335
• pcodes: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable