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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 in aqueous media, in the presence of unprotected functional groups. In addition to its compatibility, these reactions proceed relatively quickly, 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. 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. 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, demonstrating the potential for these materials in a wide variety of drug delivery applications.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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PEGylation and Dimerization of Expressed Proteins under Near Equimolar Conditions with Potassium 2-Pyridyl Acyltrifluoroborates.
White CJ, et al.
ACS central science (2017)
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)
Critical evaluation and rate constants of chemoselective ligation reactions for stoichiometric conjugations in water.
Saito, et al.
ACS Chemical Biology, 10, 1026-1033 (2015)
Alberto Osuna Gálvez et al.
Journal of the American Chemical Society, 139(5), 1826-1829 (2017-01-25)
Current methods for constructing amide bonds join amines and carboxylic acids by dehydrative couplings-processes that usually require organic solvents, expensive and often dangerous coupling reagents, and masking other functional groups. Here we describe an amide formation using primary amines and
Fumito Saito et al.
ACS chemical biology, 10(4), 1026-1033 (2015-01-13)
Chemoselective ligation reactions have contributed immensely to the development of organic synthesis and chemical biology. However, the ligation of stoichiometric amounts of large molecules for applications such as protein-protein conjugates is still challenging. Conjugation reactions need to be fast enough
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The Bode Group aims to develop new reactions and reagents for the synthesis of complex molecules. The Bode Group has developed N-mesityl-substituted NHCs as organocatalysts for the catalytic generation of reactive species including activated carboxylates, homoenolates, and enolates. These novel catalysts and reactions have made possible a new generation of highly enantioselective annulations from simple starting materials under mild reaction conditions, usually at room temperature and without added reagents. Furthering the goal of designing new reagents to enable the assembly of complex molecules, the Bode group has developed SnAP reagents for the facile, one-pot conversion of aldehydes into N-unprotected, saturated N-heterocycles, including bicyclic and spirocyclic structures. These easy to handle reagents provide a simple and robust alternative to the challenging and restrictive cross-coupling methods for the functionalization of saturated N-heterocycles.

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