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531480

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Fabian Schnitter et al.
Nature protocols, 16(8), 3901-3932 (2021-07-02)
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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)
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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