F6562
Fmoc-(R)-2-(7-octenyl)Ala-OH
for peptide synthesis
Synonym(s):
(R)-N-Fmoc-α-(7-Octenyl)alanine, Fmoc-(R)-2-(7-octenyl)alanine, Fmoc-(R)-2-amino-2-methyl-dec-6-enoic acid
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About This Item
Empirical Formula (Hill Notation):
C26H31NO4
CAS Number:
Molecular Weight:
421.53
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.26
MDL number:
Product Name
Fmoc-(R)-2-(7-octenyl)Ala-OH,
form
solid
Quality Level
reaction suitability
reaction type: Fmoc solid-phase peptide synthesis
application(s)
peptide synthesis
functional group
Fmoc
storage temp.
−20°C
SMILES string
O=C(OCC1C(C=CC=C2)=C2C3=C1C=CC=C3)N[C@@](CCCCCCC=C)(C)C(O)=O
InChI
1S/C26H31NO4/c1-3-4-5-6-7-12-17-26(2,24(28)29)27-25(30)31-18-23-21-15-10-8-13-19(21)20-14-9-11-16-22(20)23/h3,8-11,13-16,23H,1,4-7,12,17-18H2,2H3,(H,27,30)(H,28,29)/t26-/m1/s1
InChI key
MADFVGMQNXRFAF-AREMUKBSSA-N
Application
Olefinic alpha-methyl amino acid for peptide stapling. Upon incorporation of this amino acid into a peptide, along with another of the same or derivative with a different length of the olefinic side chain, the two can be ′stapled′ via a ring closing metathesis reaction with Grubb′s catalyst (product # 579726). The resulting stapled peptide macrocycle has been shown to stabilize the alpha-helical structure of peptides, which can lead to favorable biological characteristics such as increased proteolytic stability and cellular uptake.
signalword
Warning
hcodes
pcodes
Hazard Classifications
Aquatic Acute 1
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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Young-Woo Kim et al.
Nature protocols, 6(6), 761-771 (2011-06-04)
This protocol provides a detailed procedure for the preparation of stapled α-helical peptides, which have proven their potential as useful molecular probes and as next-generation therapeutics. Two crucial features of this protocol are (i) the construction of peptide substrates containing
Assessing the Efficacy of Mdm2/Mdm4-Inhibiting Stapled Peptides Using Cellular Thermal Shift Assays.
Ban Xiong Tan et al.
Scientific reports, 5, 12116-12116 (2015-07-15)
Previous publications on stapled peptide inhibitors against Mdm2/Mdm4-p53 interactions have established that this new class of drugs have the potential to be easily optimised to attain high binding affinity and specificity, but the mechanisms controlling their cellular uptake and target
Global Trade Item Number
| SKU | GTIN |
|---|---|
| F6562-5G | 04061832597805 |
| F6562-1G | 04061826097380 |