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B2559

Sigma-Aldrich

B581

>95% (HPLC), solid

Synonym(s):

N-[2(S)-(2(R)-2-Amino-3-mercaptopropylamino)-3-methylbutyl]-L-phenylalanyl-L-methionine trifluoroacetate salt

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About This Item

Empirical Formula (Hill Notation):
C22H38N4O3S2
CAS Number:
149759-96-6
Molecular Weight:
470.69
MDL number:
MFCD00236999
UNSPSC Code:
12352202
PubChem Substance ID:
24891659
NACRES:
NA.77

Assay

>95% (HPLC)

form

solid

composition

Peptide content, ~60%

color

white

solubility

H2O: soluble

storage temp.

−20°C

SMILES string

CSCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC[C@@H](NC[C@@H](N)CS)C(C)C)C(O)=O

InChI

1S/C22H38N4O3S2/c1-15(2)20(24-12-17(23)14-30)13-25-19(11-16-7-5-4-6-8-16)21(27)26-18(22(28)29)9-10-31-3/h4-8,15,17-20,24-25,30H,9-14,23H2,1-3H3,(H,26,27)(H,28,29)/t17-,18+,19+,20-/m1/s1

InChI key

QISLMXIYRQCLIR-FUMNGEBKSA-N

Gene Information

rat ... Fnta(25318)

Amino Acid Sequence

Cys-(R)-Val-(R)-Phe-Met

Biochem/physiol Actions

Stable and membrane permeable inhibitor of farnesyltransferase.

Packaging

Packaged under nitrogen and with desiccant.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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A Wagle et al.
The Journal of biological chemistry, 273(24), 14968-14974 (1998-06-17)
Glucose-6-phosphate dehydrogenase (G6PDH) controls the flow of carbon through the pentose phosphate pathway and also produces NADPH needed for maintenance of reduced glutathione and reductive biosynthesis. Hepatic expression of G6PDH is known to respond to several dietary and hormonal factors
R Roskoski et al.
Biochemistry, 40(31), 9329-9335 (2001-08-02)
Protein farnesyltransferase (FTase) and protein geranylgeranyltransferase-I (GGTase-I) catalyze the prenylation of proteins with a carboxy-terminal tetrapeptide sequence called a CaaX box, where C refers to cysteine, "a" refers to an aliphatic residue, and X typically refers to methionine, serine, or
K Yoshimatsu et al.
Gan to kagaku ryoho. Cancer & chemotherapy, 24(2), 145-155 (1997-01-01)
Posttranslational farnesylation by farnesyltransferase (FTase) is critical for the function of ras oncogene product and FTase has attracted attention as the new target of anticancer agents. B956 and B1352, obtained from the screening of CAAX analog inhibitors of FTase, induced
A M Garcia et al.
The Journal of biological chemistry, 268(25), 18415-18418 (1993-09-05)
The ras protooncogene is involved in regulation of cell growth. Mutations that activate the protein result in uncontrolled cell growth. Ras undergoes a series of posttranslational processing events, the first of which, farnesylation, is crucial for the function of the
Daniel Bakowski et al.
The Journal of physiology, 553(Pt 2), 387-393 (2003-11-05)
In many cell types, the emptying of intracellular Ca2+ stores results in the opening of store-operated Ca2+ channels in the plasma membrane. However, the nature of the signal that couples store content to the opening of these Ca2+ channels is
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