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47633

Sigma-Aldrich

Fmoc-Leu-OH

≥97.0%

Synonym(s):
N-(9-Fluorenylmethoxycarbonyl)-L-leucine, Fmoc-L-leucine
Empirical Formula (Hill Notation):
C21H23NO4
CAS Number:
Molecular Weight:
353.41
Beilstein:
2178254
EC Number:
MDL number:
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.26

Quality Level

assay

≥97.0%

optical activity

[α]20/D −25±2°, 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

152-156 °C (lit.)
152-156 °C

application(s)

peptide synthesis

functional group

Fmoc
amine
carboxylic acid

storage temp.

2-8°C

SMILES string

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

InChI

1S/C21H23NO4/c1-13(2)11-19(20(23)24)22-21(25)26-12-18-16-9-5-3-7-14(16)15-8-4-6-10-17(15)18/h3-10,13,18-19H,11-12H2,1-2H3,(H,22,25)(H,23,24)/t19-/m0/s1

InChI key

CBPJQFCAFFNICX-IBGZPJMESA-N

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Application

Fmoc-Leu-OH can be used as a reactant to synthesize:
  • Various oligopeptides by reacting with functionalized α-amino acid hydrochloride salts.
  • A cyclic depsipeptide sansalvamide A, a natural product found in marine fungus.
  • Streptocidin A−D, decapeptide antibiotics naturally found in Streptomyces sp. Tü 6071.
  • Coumaroyl dipeptide amide that can be used for cosmetic applications.

Packaging

5, 50 g in glass bottle

Biochem/physiol Actions

PPARγ ligand that induces insulin sensitization, but not adipogenesis.

Storage Class Code

13 - Non 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

Certificate of Analysis

Certificate of Origin

Facile solid-phase synthesis of cyclic decapeptide antibiotic streptocidins A-D
Qin C, et al.
Tetrahedron Letters, 45(1), 217-220 (2004)
Markus Beck Erlach et al.
Journal of biomolecular NMR, 69(2), 53-67 (2017-09-16)
For evaluating the pressure responses of folded as well as intrinsically unfolded proteins detectable by NMR spectroscopy the availability of data from well-defined model systems is indispensable. In this work we report the pressure dependence of
Catalytic Oligopeptide Synthesis
Liu Z, et al.
Organic Letters, 20(3), 612-615 (2018)
Rapid, high-yield, solid-phase synthesis of the antitumor antibiotic sansalvamide A using a side-chain-tethered phenylalanine building block
Lee Y and Silverman RB
Organic Letters, 2(23), 3743-3746 (2000)
G Cheng et al.
Langmuir : the ACS journal of surfaces and colloids, 26(7), 4990-4998 (2010-01-16)
The self-assembly and hydrogelation properties of two Fmoc-tripeptides [Fmoc = N-(fluorenyl-9-methoxycarbonyl)] are investigated, in borate buffer and other basic solutions. A remarkable difference in self-assembly properties is observed comparing Fmoc-VLK(Boc) with Fmoc-K(Boc)LV, both containing K protected by N(epsilon)-tert-butyloxycarbonate (Boc). In

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