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47633

Sigma-Aldrich

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
Beilstein:
2178254
EC Number:
MDL number:
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.26
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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.[1]
  • A cyclic depsipeptide sansalvamide A, a natural product found in marine fungus.[2]
  • Streptocidin A−D, decapeptide antibiotics naturally found in Streptomyces sp. Tü 6071.[3]
  • Coumaroyl dipeptide amide that can be used for cosmetic applications.[4]

Biochem/physiol Actions

PPARγ ligand that induces insulin sensitization, but not adipogenesis.

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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Certificates of Analysis (COA)

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Synthesis and Evaluation of Coumaroyl Dipeptide Amide as Potential Whitening Agents
Lee H-S, et al.
Bull. Korean Chem. Soc., 34(10), 3017-3021 (2013)
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
Facile solid-phase synthesis of cyclic decapeptide antibiotic streptocidins A-D
Qin C, et al.
Tetrahedron Letters, 45(1), 217-220 (2004)
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)

Questions

1–2 of 2 Questions  
  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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