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Merck
CN

37347

O-(2-Oxo-1(2H)pyridyl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate

≥99.0% (HPLC)

Synonym(s):

O-(1,2-Dihydro-2-oxo-1-pyridyl)-N,N,N′-N′-tetramethyluronium tetrafluoroborate, TPTU

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About This Item

Empirical Formula (Hill Notation):
C10H16BF4N3O2
CAS Number:
125700-71-2
Molecular Weight:
297.06
NACRES:
NA.22
PubChem Substance ID:
57649720
UNSPSC Code:
12352005
MDL number:
MFCD00075475

Key Documents

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Product Name

O-(2-Oxo-1(2H)pyridyl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate, ≥99.0% (HPLC)

InChI key

CZQGINAUZYECAI-UHFFFAOYSA-N

SMILES string

F[B-](F)(F)F.CN(C)C(\ON1C=CC=CC1=O)=[N+](/C)C

InChI

1S/C10H16N3O2.BF4/c1-11(2)10(12(3)4)15-13-8-6-5-7-9(13)14;2-1(3,4)5/h5-8H,1-4H3;/q+1;-1

assay

≥99.0% (HPLC)

reaction suitability

reaction type: Coupling Reactions

mp

140 °C (dec.) (lit.)

application(s)

peptide synthesis

functional group

amine

storage temp.

2-8°C

Quality Level

100

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Related Categories

Application

Reagent for:
Amidation
Peptide Coupling
Esterification of nucleosides to solid phase supports for oligonucleoside synthesis

Other Notes

Coupling reagent for peptide synthesis, especially suited for segment condensation with little racemization

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

hcodes

H317,H318

Hazard Classifications

Eye Dam. 1 - Skin Sens. 1A

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
1431915V
1431915
1320570
1316653
046635/1

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Tomohisa Sawada et al.
Journal of the American Chemical Society, 133(19), 7336-7339 (2011-04-28)
Artificial mimicry of α-helices offers a basis for development of protein-protein interaction antagonists. Here we report a new type of unnatural peptidic backbone, containing α-, β-, and γ-amino acid residues in an αγααβα repeat pattern, for this purpose. This unnatural
C M Huntley et al.
Nucleosides, nucleotides & nucleic acids, 20(4-7), 731-733 (2001-09-21)
The synthesis of 1-(beta-D-ribofuranosyl)pyridin-2-one-3-carboxylic acid and the 3-carboxamide as well as a short series of 3N-carboxamides, prepared by TPTU/HOBt coupling of primary amines with 1-(beta-D-ribofuranosyl)pyridin-2-one-3-carboxylic acid, and their evaluation as anti-infective agents is described.
R T Pon et al.
Bioconjugate chemistry, 10(6), 1051-1057 (1999-11-24)
Nucleosides can be esterified to solid-phase supports using uronium or phosphonium coupling reagents and a coupling additive, such as 1-hydroxybenzotriazole (HOBT), 7-aza-1-hydroxybenzotriazole (HOAT), N-methylimidazole (NMI), or 4-(dimethylamino)pyridine (DMAP). However, DMAP was far superior to other additives and high nucleoside loadings
Knorr, R, et al.
Tetrahedron Letters, 30, 1927-1927 (1989)

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