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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

signalword

Warning

hcodes

H400

Hazard Classifications

Aquatic Acute 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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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