SBAP Linker

Chemical name: N-Succinimidyl-3-(bromoacetamido) propionate // Synonyms: 2,5-dioxopyrrolidin-1-yl 3-(2-bromoacetamido)propanoate, 2-bromo-N-[3-[(2,5-dioxo-1-pyrrolidinyl)oxy]-3-oxopropyl]-acetamide, N-(2-Bromoacetyl)-ß-alanine 2,5-dioxo-1-pyrrolidinyl ester, SBAP

  • Product code:RL-3590
  • CAS No.:57159-62-3
  • Formula:C9H11BrN2O5
  • Molecular weight:307,10 g/mol
Grouped product items
Qty Packing unit Price SKU
1 g
$405.00
RL-3590.0001
5 g
$1,620.00
RL-3590.0005
Safety Data Sheets
description

The non-cleavable, heterobifunctional linker SBAP is reactive towards sulfhydryl- (at pH >7.5) and amino-groups (at pH 7-9) via its bromoacetyl and NHS-ester moiety, respectively, for form the corresponding thioether and amide bonds. This reagent has been used for the preparation of cyclic peptides and peptide conjugates as the spacer allows to keep a peptide-like character in the crosslinked species.


references

Effects of Conformational Changes in Peptide-CRM197 Conjugate Vaccines; J. Jaffe, K. Wucherer, J. Sperry, Q. Zou, Q. Chang, M. A. Massa, K. Bhattacharya, S. Kumar, M. Caparon, D. Stead, P. Wrigth, A. Dirksen, M. B. Francis; Bioconjug Chem. 2019; 30(1): 47-53. https://doi.org/10.1021/acs.bioconjchem.8b00661.

Investigation of Hydrophilic Auristatin Derivatives for Use in Antibody Drug Conjugates; B. A. Mendelsohn, S. D. Barnscher, J. T. Snyder, Z. An, J. M. Dodd, J. Dugal-Tessier; Bioconjugate Chem. 2017; 28(2): 371-381. https://doi.org/10.1021/acs.bioconjchem.6b00530.

Oligosaccharide conjugates of Bordetella pertussis and bronchiseptica induce bactericidal antibodies, an addition to pertussis vaccine; J. Kubler-Kielb, E. Vinogradov, T. Lagergård, A. Ginzberg, J. D. King, A. Preston, D. J. Maskell, V. Pozsgay, J. M. Keith, J. B. Robbins, R. Schneerson; PNAS 2011; 108(10): 4087-4092. https://doi.org/10.1073/pnas.1100782108.

Effect of the nonreducing end of Shigella dysenteriae type 1 O-specific oligosaccharides on their immunogenicity as conjugates in mice; V. Pozsgay, J. Kubler-Kielb, R. Schneerson, J. B. Robbins; PNAS 2007; 104(36): 14478-14482. https://doi.org/10.1073/pnas.0706969104.

Long-lastng and transmission-blocking activity of antibodies to Plasmodium falciparum elicited in mice by protein conjugates of Pfs25; J. Kubler-Kielb, F. Majadly, Y. Wu, D. L. Narum, C. Guo, L. H. Miller, J. Shiloach, J. B. Robbins, R. Schneerson; PNAS 2007; 104(1): 293-298. https://doi.org/10.1073/pnas.0609885104.

A New Method for Conjugation of Carbohydrates to Proteins Using an Aminooxy-Thiol Heterobifunctional Linker; J. Kubler-Kielb, V. Pozsgay; J. Org. Chem. 2005; 70(17): 6987-6990. https://doi.org/10.1021/jo050934b.

Synthesis of a dimeric Lewis antigen and the evaluation of the epitope specificity of antibodies elicited in mice; T. Buskas, Y. Li, G.-J. Boons; Chem Eur J. 2005; 11(18): 5457-67. https://doi.org/10.1002/chem.200500412.

Cellular Uptake of Antisense Morpholino Oligomers Conjugated to Arginine-Rich Peptides; H. M. Moulton, M. H. Nelson, S. A. Hatlevig, M. T. Reddy, P. L. Iversen; Bioconjugate Chem. 2004; 15(2): 290-299. https://doi.org/10.1021/bc034221g.

The Generality of DNA-Templated Synthesis as a Basis for Evolving Non-Natural Small Molecules; Z. J. Gartner, D. R. Liu; J. Am. Chem. Soc. 2001; 123(28): 6961-6963. https://doi.org/10.1021/ja015873n.


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