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15035

Sigma-Aldrich

(Boc-aminooxy)acetic acid

≥98.0% (T)

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Synonym(s):
N-Boc-(carboxymethoxy)amine
Linear Formula:
(CH3)3CO2CNHOCH2CO2H
CAS Number:
Molecular Weight:
191.18
Beilstein/REAXYS Number:
6137646
MDL number:
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

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(Boc-aminooxy)acetic acid ≥98.0% (T)

15035

(Boc-aminooxy)acetic acid

Boc-2-Abz-OH ≥98.0% (T)

15297

Boc-2-Abz-OH

Boc-Tle-OH ≥99.0% (T)

15451

Boc-Tle-OH

Boc-6-Ahx-OSu ≥98.0% (TLC)

15661

Boc-6-Ahx-OSu

Quality Level

200

Quality Level

-

Quality Level

100

Quality Level

100

mp

~115 °C (dec.)

mp

153-156 °C (dec.)

mp

118-121 °C

mp

86-90 °C

form

powder

form

-

form

-

form

-

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

11 - Combustible Solids

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves


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O. Nyanguile et al.
Lett. Pept. Sci., 1, 9-9 (1994)
Mariarosaria De Simone et al.
Contrast media & molecular imaging, 11(6), 561-571 (2017-01-05)
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
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)
Rory K Morgan et al.
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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