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Sigma-Aldrich

SBAP (succinimidyl 3-(bromoacetamido)propionate)

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Empirical Formula (Hill Notation):
C9H11N2O5Br
CAS Number:
57159-62-3
Molecular Weight:
307.10
MDL number:
MFCD01863457
UNSPSC Code:
12352200
PubChem Substance ID:
329768824
NACRES:
NA.22

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

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

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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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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