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Key Documents

15035

Sigma-Aldrich

(Boc-aminooxy)acetic acid

≥98.0% (T)

Synonym(s):

N-Boc-(carboxymethoxy)amine

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About This Item

Linear Formula:
(CH3)3CO2CNHOCH2CO2H
CAS Number:
Molecular Weight:
191.18
Beilstein:
6137646
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

≥98.0% (T)

form

powder

mp

~115 °C (dec.)

SMILES string

CC(C)(C)OC(=O)NOCC(O)=O

InChI

1S/C7H13NO5/c1-7(2,3)13-6(11)8-12-4-5(9)10/h4H2,1-3H3,(H,8,11)(H,9,10)

InChI key

QBXODCKYUZNZCY-UHFFFAOYSA-N

Related Categories

Application

(Boc-aminooxy)acetic acid was used in the preparation of Boc-aminooxy tetra(ethylene glycol).

Other Notes

Employed to introduce a hydroxylamine moiety into peptides; reaction with an aldehyde to an oxime.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Site-specific protein immobilization through N-terminal oxime linkages.
Journal of Materials Chemistry, 17(19), 2021-2027 (2007)
J. Shao et al.
Journal of the American Chemical Society, 117, 3893-3893 (1995)
O. Nyanguile et al.
Lett. Pept. Sci., 1, 9-9 (1994)
Mariarosaria De Simone et al.
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Superparamagnetic iron oxide nanoparticles (SPIONs) have received increasing interest as contrast media in biomedical imaging and innovative therapeutic tools, in particular for loco-regional ablative treatments and drug delivery. The future of therapeutic applications would strongly benefit from improving the capability
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ACS chemical biology, 10(8), 1778-1784 (2015-05-16)
ADP-ribosylation is essential for cell function, yet there is a dearth of methods for detecting this post-translational modification in cells. Here, we describe a clickable aminooxy alkyne (AO-alkyne) probe that can detect cellular ADP-ribosylation on acidic amino acids following Cu-catalyzed

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