ANP-Linker
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ANP-Linker

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Category
Fmoc-Amino Acids
Catalog number
BAT-008874
CAS number
171778-06-6
Molecular Formula
C24H20N2O6
Molecular Weight
432.4
ANP-Linker
IUPAC Name
3-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(2-nitrophenyl)propanoic acid
Synonyms
Fmoc-3-amino-3-(2-nitro-penyl)-propionic acid; Fmoc-D-beta-Phe(2-NO2)-OH
Purity
95%
Density
1.37 g/cm3
Melting Point
193-202 °C
Boiling Point
695.5 °C at 760 mmHg
InChI
InChI=1S/C24H20N2O6/c27-23(28)13-21(19-11-5-6-12-22(19)26(30)31)25-24(29)32-14-20-17-9-3-1-7-15(17)16-8-2-4-10-18(16)20/h1-12,20-21H,13-14H2,(H,25,29)(H,27,28)
InChI Key
DRESTDPDCGPKNI-UHFFFAOYSA-N
Canonical SMILES
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC(=O)O)C4=CC=CC=C4[N+](=O)[O-]
1.A single-bead decode strategy using electrospray ionization mass spectrometry and a new photolabile linker: 3-amino-3-(2-nitrophenyl)propionic acid.
Brown BB1, Wagner DS, Geysen HM. Mol Divers. 1995 Sep;1(1):4-12.
A new linker that employs a photosensitive 3-amino-3-(2-nitrophenyl)propionyl functionality (ANP-resin) has been developed for the preparation of C-terminal carboxamides. A wide range of carboxamides were prepared and identified using the ANP-resin and electrospray ionization mass spectrometry. A single bead containing tripeptide Fmoc-Asp-Arg(Tos)-Val-NH2 was isolated, photocleaved and the peptide was characterized by tandem mass spectrometry, thereby verifying a library decode strategy that avoids complex tagging procedures.
2.Selective capture and collection of live target cells using a photoreactive silicon wafer device modified with antibodies via a photocleavable linker.
Ariyasu S1, Hanaya K, Watanabe E, Suzuki T, Horie K, Hayase M, Abe R, Aoki S. Langmuir. 2012 Sep 11;28(36):13118-26. doi: 10.1021/la302393p. Epub 2012 Aug 29.
A device for the capture and recollection of live target cells is described. The platform was a silicon (Si) wafer modified with an anti-HEL antibody (anti-HEL-IgG, HEL = hen egg lysozyme) through a photocleavable 3-amino-3-(2-nitrophenyl)propionic acid (ANP) linker. The modification processes of the Si wafer surface were monitored by Fourier transform infrared spectroscopy-attenuated total reflection (FTIR-ATR) and fast-scanning atomic force microscopy (FS-AFM). The attachment of IgG and its release reaction on the Si surface via the photochemical cleavage of the ANP linker were observed directly by FS-AFM. The results of an enzyme-linked immunosorbent assay (ELISA) indicated that the photorelease of the complex of anti-HEL-IgG with the secondary antibody-alkaline phosphatase hybrid (secondary IgG-AP) from the Si surface occurs with minimum damage. Furthermore, it was possible to collect SP2/O cells selectively that express HEL on their cell membranes (SP2/O-HEL) on the Si wafer device.
3.Atrial natriuretic peptide-Fc, ANP-Fc, fusion proteins: semisynthesis, in vitro activity and pharmacokinetics in rats.
Mezo AR1, McDonnell KA, Low SC, Song J, Reidy TJ, Lu Q, Amari JV, Hoehn T, Peters RT, Dumont J, Bitonti AJ. Bioconjug Chem. 2012 Mar 21;23(3):518-26. doi: 10.1021/bc200592c. Epub 2012 Feb 14.
Atrial natriuretic peptide (ANP) may be a useful molecule for the treatment of cardiovascular diseases due to its potent natriuretic effects. In an effort to prolong the short in vivo half-life of ANP, fusions of the peptide to the Fc domain of IgG were generated using a semisynthetic methodology. Synthetic ANP peptides were synthesized with thioesters at either the N- or C-termini of the peptide and subsequently linked to the N-terminus of recombinantly expressed Fc using native chemical ligation. The linker length between the ANP and Fc moieties was varied among 2, 11, or 16 amino acids. In addition, either one ("monomeric") or two ("dimeric") ANP peptides were linked to Fc to study whether this modification had an effect on in vitro activity and/or in vivo half-life. The various constructs were studied for in vitro activity using a cell-based cGMP assay. The ANP-Fc fusion constructs were between 16- and ∼375-fold weaker than unconjugated ANP in this assay, and a trend was observed where the most potent conjugates were those with longer linkers and in the dimeric configuration.
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