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F6062

Sigma-Aldrich

Fmoc-(S)-2-(2-propenyl)Ala-OH

Synonym(s):

(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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About This Item

Empirical Formula (Hill Notation):
C21H21NO4
CAS Number:
288617-71-0
Molecular Weight:
351.40
MDL number:
MFCD02682444
UNSPSC Code:
12352200
PubChem Substance ID:
329799749
NACRES:
NA.26

Assay

≥97%

Quality Level

200

form

solid

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@](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

InChI key

FNCSRFHDUZYOCR-NRFANRHFSA-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.

Pictograms

Environment
GHS09

Signal Word

Warning

Hazard Statements

H400

Precautionary Statements

P273 - P391 - P501

Hazard Classifications

Aquatic Acute 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SLBH5603V

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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

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