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Sigma-Aldrich

Fmoc-Arg(Pbf)-OH

≥98.0% (HPLC)

Synonym(s):

Nα-Fmoc-Nω-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-L-arginine, Nα-Fmoc-Nω-Pbf-L-arginine

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About This Item

Empirical Formula (Hill Notation):
C34H40N4O7S
CAS Number:
154445-77-9
Molecular Weight:
648.77
Beilstein/REAXYS Number:
8302671
MDL number:
MFCD00235804
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
57650929
NACRES:
NA.26

Quality Level

100

assay

≥98.0% (HPLC)

form

powder or crystals

optical activity

[α]/D -5.5±1.0°, c = 1 in DMF

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

application(s)

peptide synthesis

functional group

Fmoc

storage temp.

−20°C

SMILES string

Cc1c(C)c(c(C)c2CC(C)(C)Oc12)S(=O)(=O)NC(=N)NCCC[C@H](NC(=O)OCC3c4ccccc4-c5ccccc35)C(O)=O

InChI

1S/C34H40N4O7S/c1-19-20(2)30(21(3)26-17-34(4,5)45-29(19)26)46(42,43)38-32(35)36-16-10-15-28(31(39)40)37-33(41)44-18-27-24-13-8-6-11-22(24)23-12-7-9-14-25(23)27/h6-9,11-14,27-28H,10,15-18H2,1-5H3,(H,37,41)(H,39,40)(H3,35,36,38)/t28-/m0/s1

InChI key

HNICLNKVURBTKV-NDEPHWFRSA-N

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General description

Fmoc-Arg(Pbf)-OH is used as a building block in peptide synthesis, providing protection to specific functional groups while allowing for efficient peptide bond formation.

Application

Fmoc-Arg(Pbf)-OH is a Fmoc-protected amino acid derivative that can be used to create arginine-containing peptides. The 2,2,4,6,7-pentamethyIdlhydrobenzofuran-5-sulfonyl group (Pbf) can be easily cleaved by trifluoroacetic acid (TFA).

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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The 2, 2, 4, 6, 7-pentamethyldihydrobenzofuran-5-sulfonyl group (Pbf) as arginine side chain protectant.
Carpino L A, et al.
Tetrahedron Letters, 34(49), 7829-7832 (1993)
Solid phase synthesis, radiolabeling and biological evaluation of a 99mTc-labeled αVβ3 tripeptide (RGD) conjugated to DOTA as a tumor imaging agent.
Varshney R, et al.
Cancer Biology & Therapy, 11(10), 893-901 (2011)
Synthesis of positional-scanning libraries of fluorogenic peptide substrates to define the extended substrate specificity of plasmin and thrombin.
Backes B J, et al.
Nature Biotechnology, 18(2), 187-187 (2000)
A cobaltocenium?peptide bioconjugate shows enhanced cellular uptake and directed nuclear delivery.
Noor F, et al.
Angewandte Chemie (International Edition in English), 44(16), 2429-2432 (2005)
Enhancement of the T140-based pharmacophores leads to the development of more potent and bio-stable CXCR4 antagonists.
Tamamura H, et al.
Organic & Biomolecular Chemistry, 1(21), 3663-3669 (2003)
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