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Sigma-Aldrich

Fmoc-Ala-OH

95%, for peptide synthesis

Synonym(s):

N-(9-Fluorenylmethoxycarbonyl)-L-alanine, Fmoc-L-alanine

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About This Item

Empirical Formula (Hill Notation):
C18H17NO4
CAS Number:
Molecular Weight:
311.33
Beilstein:
2225975
EC Number:
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.26

product name

Fmoc-Ala-OH, 95%

Quality Level

Assay

95%

optical activity

[α]20/D −18°, c = 1 in DMF

reaction suitability

reaction type: C-H Activation
reaction type: Fmoc solid-phase peptide synthesis
reagent type: ligand
reaction type: Peptide Synthesis

mp

147-153 °C (lit.)

application(s)

peptide synthesis

functional group

Fmoc
amine
carboxylic acid

storage temp.

2-8°C

SMILES string

C[C@H](NC(=O)OCC1c2ccccc2-c3ccccc13)C(O)=O

InChI

1S/C18H17NO4/c1-11(17(20)21)19-18(22)23-10-16-14-8-4-2-6-12(14)13-7-3-5-9-15(13)16/h2-9,11,16H,10H2,1H3,(H,19,22)(H,20,21)/t11-/m0/s1

InChI key

QWXZOFZKSQXPDC-NSHDSACASA-N

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General description

Fmoc-Ala-OH also known as Fmoc-L-alanine, is a versatile reagent used in Fmoc solid-phase peptide synthesis.

Application

Fmoc-Ala-OH is commonly used :
  • as a building block in the preparation of triazolopeptides , and azapeptides
  • in the synthesis of bis-cationic porphyrin peptides using the standard Fmoc solid-phase synthesis
  • to transform Mannich-adducts into α-halogenated amides without undergoing aziridination

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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Towards sequence selective DNA binding: design, synthesis and DNA binding studies of novel bis-porphyrin peptidic nanostructures
E Biron
Organic & Biomolecular Chemistry, 6, 2507-2515 (2008)
Fabian Schnitter et al.
Nature protocols, 16(8), 3901-3932 (2021-07-02)
Many supramolecular materials in biological systems are driven to a nonequilibrium state by the irreversible consumption of high-energy molecules such as ATP or GTP. As a result, they exhibit unique dynamic properties such as a tunable lifetime, adaptivity or the
Substrate-derived triazolo-and azapeptides as inhibitors of cathepsins K and S
M Galibert
European Journal of Medicinal Chemistry, 144, 201-210 (2018)
? -Halo amides as competent latent enolates: direct catalytic asymmetric Mannich-type reaction
B Sun
Journal of the American Chemical Society, 139, 8295-8301 (2017)
Xue Zhi Zhao et al.
Molecules (Basel, Switzerland), 23(8) (2018-07-28)
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