F6062
Fmoc-(S)-2-(2-propenyl)Ala-OH
别名:
(S)-N-Fmoc-α-2-n-propenylalanine, Fmoc-(S)-2-(2-propenyl)alanine, Fmoc-(S)-2-amino-2-methyl-4-pentenoic acid
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关于此项目
经验公式（希尔记法）:
C21H21NO4
化学文摘社编号:
分子量:
351.40
NACRES:
NA.26
PubChem Substance ID:
UNSPSC Code:
12352200
MDL number:
InChI key
FNCSRFHDUZYOCR-NRFANRHFSA-N
SMILES string
O=C(OCC1C(C=CC=C2)=C2C3=C1C=CC=C3)N[C@](CC=C)(C)C(O)=O
InChI
1S/C21H21NO4/c1-3-12-21(2,19(23)24)22-20(25)26-13-18-16-10-6-4-8-14(16)15-9-5-7-11-17(15)18/h3-11,18H,1,12-13H2,2H3,(H,22,25)(H,23,24)/t21-/m0/s1
assay
≥97%
form
solid
reaction suitability
reaction type: Fmoc solid-phase peptide synthesis
application(s)
peptide synthesis
functional group
Fmoc
storage temp.
−20°C
Quality Level
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
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
法规信息
新产品
此项目有
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
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