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B2682

Sigma-Aldrich

Boc-Asp(OMe)-fluoromethyl ketone

≥90% (TLC), solid

Synonym(s):

Boc-D-FMK

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About This Item

Empirical Formula (Hill Notation):
C11H18NO5F
CAS Number:
187389-53-3
Molecular Weight:
263.26
MDL number:
MFCD03453073
UNSPSC Code:
12352209
PubChem Substance ID:
329773206
NACRES:
NA.77

assay

≥90% (TLC)

form

solid

solubility

DMF: soluble

storage temp.

−20°C

SMILES string

COC(=O)C[C@H](NC(=O)OC(C)(C)C)C(=O)CF

InChI

1S/C11H18FNO5/c1-11(2,3)18-10(16)13-7(8(14)6-12)5-9(15)17-4/h7H,5-6H2,1-4H3,(H,13,16)/t7-/m0/s1

InChI key

MXOOUCRHWJYCAL-ZETCQYMHSA-N

Application

Boc-Asp(OMe)-fluoromethyl ketone (Boc-D-fmk) has been used as a caspase inhibitor to study its effects on lactate dehydrogenase (LDH) leakage, apoptosis and virus proliferation in chorion cells , as a component of the transplantation medium for the transplantation of human embryonic stem cells (ESC)-derived medial ganglionic eminence (MGE) cells into hippocampus of mice , as a protease inhibitor to study its effects on cell death in parasites .

Biochem/physiol Actions

Boc-Asp(OMe)-fluoromethyl ketone (Boc-D-fmk) permits cell permeability. It is a caspase inhibitor and suppresses apoptosis induced by various kinds of stimuli. Boc-D-fmk poorly inhibits caspases-2, -5, -6 and -10.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H319

Hazard Classifications

Eye Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Lactate dehydrogenase leakage as a marker for apoptotic cell degradation induced by influenza virus infection in human fetal membrane cells
Uchide N, et al.
Intervirology, 52(3), 164-173 (2009)
Heat-induced programmed cell death in Leishmania infantum is reverted by Bcl-X L expression
Alzate JF, et al.
Apoptosis, 11(2), 161-171 (2006)
Differentiation of human pluripotent stem cells into Medial Ganglionic Eminence vs. Caudal Ganglionic Eminence cells
Ahn S, et al.
Methods, 101(3), 103-112 (2016)
Caspase-independent cell death induced by anti-CD2 or staurosporine in activated human peripheral T lymphocytes
Deas O, et al.
Journal of immunology (Baltimore, Md. : 1950), 161(7), 3375-3383 (1998)
Y M Chan et al.
Neuroreport, 12(3), 541-545 (2001-03-10)
Following ventral root avulsion in neonatal animals, the degeneration of spinal motoneurons occurs by an apoptotic-like morphological pathway. In adult animals, however, the mechanism of degeneration of injured motoneurons is still controversial. Because caspases are important mediators of apoptosis, we
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