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901635

Sigma-Aldrich

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

PEG average Mn 10,000

Synonyme(s) :

KAT PEG, bis KAT PEG, di KAT PEG

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About This Item

Formule linéaire :
(C6H3BF3KNO)O[CH2CH2O]nCH2CH2O(C6H3BF3KNO)
Code UNSPSC :
12352005
Nomenclature NACRES :
NA.23

Forme

powder or solid

Poids mol.

PEG average Mn 10,000
PEG ~10,000 Da

Couleur

off-white to pale yellow

Température de stockage

2-8°C

Description générale

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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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)
Critical evaluation and rate constants of chemoselective ligation reactions for stoichiometric conjugations in water.
Saito, et al.
ACS Chemical Biology, 10, 1026-1033 (2015)
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
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
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