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Merck
CN

47633

Fmoc-Leu-OH

≥97.0%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C21H23NO4
CAS Number:
Molecular Weight:
353.41
NACRES:
NA.26
PubChem Substance ID:
eCl@ss:
32160406
UNSPSC Code:
12352209
EC Number:
252-662-7
MDL number:
Beilstein/REAXYS Number:
2178254
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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

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

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.

Biochem/physiol Actions

PPARγ ligand that induces insulin sensitization, but not adipogenesis.


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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)



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Facile solid-phase synthesis of cyclic decapeptide antibiotic streptocidins A-D
Qin C, et al.
Tetrahedron Letters, 45(1), 217-220 (2004)
M J Miller et al.
The Journal of pharmacology and experimental therapeutics, 266(1), 468-472 (1993-07-01)
Anti-inflammatory properties have been ascribed to a series of N-(fluorenyl-9-methoxycarbonyl) amino acids called leumedins that inhibit the activity of granulocytes and T-lymphocytes. We evaluated one of these leumedins, N-(fluorenyl-9-methoxycarbonyl) leucine (NPC 15199), in a model of ileitis in guinea pigs.
C R Jan et al.
The Chinese journal of physiology, 43(1), 29-33 (2000-06-17)
This report demonstrates that NPC-15199 [(N-(9-fluorenylmethoxycarbonyl)L-leucine)], a novel anti-inflammatory agent, increases intracellular Ca2+ concentration ([Ca2+]i) in human bladder female transitional cancer (BFTC) cells. Using fura-2 as a Ca2+ probe, NPC-15199 (0.1-2 mM) was found to increase [Ca2+]i concentration-dependently. The response



Global Trade Item Number

SKUGTIN
47633-50G-F04061832362366
47633-5G-F04061832642581
47633-1KG-F04061826222744
47633-250G-F04061832362359