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47638

Sigma-Aldrich

Fmoc-Val-OH

≥98.0% (HPLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C20H21NO4
CAS Number:
Molecular Weight:
339.39
Beilstein:
2177443
EC Number:
MDL number:
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.26

Assay

≥98.0% (HPLC)

form

solid

optical activity

[α]20/D −17±1°, 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

143-145 °C (lit.)
143-147 °C

application(s)

peptide synthesis

functional group

Fmoc
amine
carboxylic acid

storage temp.

2-8°C

SMILES string

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

InChI

1S/C20H21NO4/c1-12(2)18(19(22)23)21-20(24)25-11-17-15-9-5-3-7-13(15)14-8-4-6-10-16(14)17/h3-10,12,17-18H,11H2,1-2H3,(H,21,24)(H,22,23)/t18-/m0/s1

InChI key

UGNIYGNGCNXHTR-SFHVURJKSA-N

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General description

Fmoc-Val-OH also known as Fmoc-L-valine, is a versatile reagent used in the Fmoc Solid-phase peptide synthesis.

Application

Fmoc-Val-OH can be used as a starting material to synthesize:
  • difficult sequence-containing pentapeptides using O-acyl isodipeptide unit
  • peptides by backbone amide linker (BAL) strategy via Fmoc Solid-phase synthesis

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

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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Backbone amide linker (BAL) strategy for N?-9-fluorenylmethoxycarbonyl (Fmoc) solid-phase synthesis of peptide aldehydes
JC Kappel
Journal of Peptide Science, 11, 525-535 (2005)
O-Acyl isopeptide method?for the efficient synthesis of difficult sequence-containing peptides: use of `O-acyl isodipeptide unit
Y Sohma
Tetrahedron Letters, 47, 3013-3017 (2006)
Rosanna Capparelli et al.
PloS one, 4(9), e7191-e7191 (2009-09-29)
Temporins are antimicrobial peptides secreted by the granular glands of the European red frog (Rana temporaria). They are 10-14 amino acid long polypeptides active prevalently against gram positive bacteria. This study shows that a synthetic temporin B analogue (TB-YK), acquires
Shih-Hurng Loh et al.
Peptides, 126, 170236-170236 (2019-12-25)
The regulation of intracellular pH (pHi) plays a vital role in various cellular functions. We previously demonstrated that three different acid extruders, the Na+-H+ exchanger (NHE), Na+-HCO3- co-transporter (NBC) and H+-linked monocarboxylate transporter (MCT), functioned together in cultured human radial
Karthik Nadendla et al.
Molecular pharmaceutics, 16(7), 2922-2928 (2019-05-24)
We have previously described the photoactivated depot (PAD) approach for the light-stimulated release of therapeutic proteins such as insulin. The aim of this method is to release insulin from a shallow dermal depot in response to blood glucose information, using

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