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901635

Sigma-Aldrich

Poly(ethylene glycol) bis(2-pyridyl KAT)

PEG average Mn 10,000

Synonym(s):

KAT PEG, bis KAT PEG, di KAT PEG

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About This Item

Linear Formula:
(C6H3BF3KNO)O[CH2CH2O]nCH2CH2O(C6H3BF3KNO)
UNSPSC Code:
12352005
NACRES:
NA.23

form

powder or solid

mol wt

PEG average Mn 10,000
PEG ~10,000 Da

color

off-white to pale yellow

storage temp.

2-8°C

General description

Poly(ethylene glycol) bis(2-pyridyl KAT) is a homobifunctional PEG featuring terminal potassium acyltrifluoroborate reactive groups for facile, rapid functionalization. Potassium acyltrifluoroborates (KATs) are stable functional groups that undergo rapid amide-forming ligations with hydroxylamines[1][2] in aqueous media, in the presence of unprotected functional groups. In addition to its compatibility, these reactions proceed relatively quickly[3], lending to their use with sensitive biological reagents. This conjugation reaction offers a new approach to the synthesis of complex molecules without the complication of side reactions, such protein-polymer conjugates[4]. KATs also undergo amide or imide-forming ligations in acidic conditions when reacted with primary amines or amides, respectively, as an alternative to classical acylation chemistry[5]. Poly(ethylene glycol) bis(2-pyridyl KAT)s have been recently used in the rapid PEGylation and dimerization of expressed, folded protiens in near equimolar conditions[6], demonstrating the potential for these materials in a wide variety of drug delivery applications.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Critical evaluation and rate constants of chemoselective ligation reactions for stoichiometric conjugations in water.
Saito, et al.
ACS Chemical Biology, 10, 1026-1033 (2015)
Potassium Acyltrifluoroborate (KAT) Ligations are Orthogonal to Thiol-Michael and SPAAC Reactions: Covalent Dual Immobilization of Proteins onto Synthetic PEG Hydrogels.
Mazunin D, et al.
Helvetica Chimica Acta, 100(2) (2017)
PEGylation and Dimerization of Expressed Proteins under Near Equimolar Conditions with Potassium 2-Pyridyl Acyltrifluoroborates.
White CJ, et al.
ACS central science (2017)
Amide-forming ligation of acyltrifluoroborates and hydroxylamines in water.
Aaron M Dumas et al.
Angewandte Chemie (International ed. in English), 51(23), 5683-5686 (2012-04-28)
Hidetoshi Noda et al.
Journal of the American Chemical Society, 136(15), 5611-5614 (2014-04-02)
The identification of fast, chemoselective bond-forming reactions is one of the major contemporary challenges in chemistry. We show that chemoselective amide-forming ligations of potassium acyltrifluoroborates (KATs) and O-carbamoylhydroxylamines proceed in the presence of all unprotected functional groups with a second-order
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