803650
SBAP (succinimidyl 3-(bromoacetamido)propionate)
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About This Item
Empirical Formula (Hill Notation):
C9H11N2O5Br
CAS Number:
Molecular Weight:
307.10
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352106
MDL number:
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)
SMILES string
O=C(CCC1=O)N1OC(CCNC(CBr)=O)=O
InChI key
WGMMKWFUXPMTRW-UHFFFAOYSA-N
assay
≥90%
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
Quality Level
Related Categories
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
Disclaimer
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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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J K Inman et al.
Bioconjugate chemistry, 2(6), 458-463 (1991-11-01)
A new amino acid derivative, N alpha-(tert-butoxycarbonyl)-N epsilon-[N-(bromoacetyl)-beta-alanyl]-L-lysine (BBAL), has been synthesized as a reagent to be used in solid-phase peptide synthesis for introducing a side-chain bromoacetyl group at any desired position in a peptide sequence. The bromoacetyl group subsequently
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