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901644

Sigma-Aldrich

Methoxy poly(ethylene glycol) KAT

PEG average Mn 5,000

Synonym(s):

KAT PEG 5k, mPEG KAT

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About This Item

Linear Formula:
H3CO[CH2CH2O]nCH2CH2O(C6H3BF3KNO)
UNSPSC Code:
51171641
NACRES:
NA.23

form

powder or solid

mol wt

PEG average Mn 5,000
PEG ~5,000 Da

color

off-white to pale yellow

storage temp.

2-8°C

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General description

Methoxy poly(ethylene glycol) 2-pyridyl KAT 5K (mPEG KAT 5K) is a monofunctional, methyl ether PEG featuring a terminal potassium acyltrifluoroborate 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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

901644-500MG:
901644-VAR:
901644-BULK:

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Critical evaluation and rate constants of chemoselective ligation reactions for stoichiometric conjugations in water.
Saito F, et al.
ACS Chemical Biology, 10, 1026-1033 (2016)
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)
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
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)
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