5-Azidopentanoic acid
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5-Azidopentanoic acid

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Useful in Click Chemistry by facilitating the cyclization of peptides.

Category
Azido Amino Acids
Catalog number
BAT-001262
CAS number
79583-98-5
Molecular Formula
C5H9N3O2
Molecular Weight
143.15
5-Azidopentanoic acid
IUPAC Name
5-azidopentanoic acid
Synonyms
5-Azidovalerianic acid
Appearance
Colorless to yellow liquid
Purity
≥ 98 %
Density
1.142 g/cm3
Boiling Point
85 ℃ at 0.01 mmHg (lit.)
Storage
Store at -20 ℃
InChI
InChI=1S/C5H9N3O2/c6-8-7-4-2-1-3-5(9)10/h1-4H2,(H,9,10)
InChI Key
SBZDIRMBQJDCLB-UHFFFAOYSA-N
Canonical SMILES
C(CCN=[N+]=[N-])CC(=O)O
1. Coiled coil peptides as universal linkers for the attachment of recombinant proteins to polymer therapeutics
Michal Pechar, Robert Pola, Richard Laga, Karel Ulbrich, Lucie Bednárová, Petr Maloň, Irena Sieglová, Vlastimil Král, Milan Fábry, Ondřej Vaněk Biomacromolecules. 2011 Oct 10;12(10):3645-55. doi: 10.1021/bm200897b. Epub 2011 Aug 31.
We have designed, synthesized, and characterized peptides containing four repeats of the sequences VAALEKE (peptide E) or VAALKEK (peptide K). While the peptides alone adopt in aqueous solutions a random coil conformation, their equimolar mixture forms heterodimeric coiled coils as confirmed by CD spectroscopy. 5-Azidopentanoic acid was connected to the N-terminus of peptide E via a short poly(ethylene glycol) spacer. The terminal azide group enabled conjugation of the peptide with a synthetic drug carrier based on the N-(2-hydroxypropyl)methacrylamide copolymer containing propargyl groups using "click" chemistry. When incorporated into the polymer drug carrier, peptide E formed a stable noncovalent complex with peptide K belonging to a recombinant single-chain fragment (scFv) of the M75 antibody. The complex thereby mediates a noncovalent linkage between the polymer drug carrier and the protein. The recombinant scFv antibody fragment was selected as a targeting ligand against carbonic anhydrase IX-a marker overexpressed by tumor cells of various human carcinomas. The antigen binding affinity of the polymer-scFv complex was confirmed by ELISA. This approach offers a well-defined, specific, and nondestructive universal method for the preparation of protein (antibody)-targeted polymer drug and gene carriers designed for cell-specific delivery.
2. Fluorescent probes of the apoptolidins and their utility in cellular localization studies
Sean M DeGuire, et al. Angew Chem Int Ed Engl. 2015 Jan 12;54(3):961-4. doi: 10.1002/anie.201408906. Epub 2014 Nov 27.
Apoptolidin A has been described among the top 0.1% most-cell-selective cytotoxic agents to be evaluated in the NCI 60 cell line panel. The molecular structure of apoptolidin A consists of a 20-membered macrolide with mono- and disaccharide moieties. In contrast to apoptolidin A, the aglycone (apoptolidinone) shows no cytotoxicity (>10 μM) when evaluated against several tumor cell lines. Apoptolidin H, the C27 deglycosylated analogue of apoptolidin A, displayed sub-micromolar activity against H292 lung carcinoma cells. Selective esterification of apoptolidins A and H with 5-azidopentanoic acid afforded azido-functionalized derivatives of potency equal to that of the parent macrolide. They also underwent strain-promoted alkyne-azido cycloaddition reactions to provide access to fluorescent and biotin-functionalized probes. Microscopy studies demonstrate apoptolidins A and H localize in the mitochondria of H292 human lung carcinoma cells.
3. 18F-labeling and initial in vivo evaluation of a Hitomi peptide for imaging tissue transglutaminase 2
Uwe Ackermann, Luise Jäger, Angela Rigopoulos, Ingrid Julienne Georgette Burvenich, Graeme Joseph O'Keefe, Andrew M Scott Nucl Med Biol. 2023 Jan-Feb;116-117:108308. doi: 10.1016/j.nucmedbio.2022.11.002. Epub 2022 Nov 26.
Introduction: Tissue transglutaminase 2 (TG2) is a calcium-dependent enzyme which cross-links proteins. It is overexpressed in many diseases and plays a key role in tissue remodeling, including cell adhesion and migration. Overexpression of TG2 in breast cancer is a marker for patients at risk of recurrence. Non-invasive imaging of TG2 can therefore play an important role in patient management. TG2 probes labeled with the positron emitters 11C and 18F have thus far not found widespread application due to purity and metabolism issues. Our approach was to radiolabel a TG2 selective, 13-mer amino acid peptide, which was modified with a 5-azidopentanoic acid group at the N-terminus via a copper free click chemistry approach. Methods: Radiochemistry was performed and fully automated using an iPhase FlexLab module. We produced the radiolabeling synthon [18F]FBz-DBCO from [18F]SFB and DBCO-amine. After HPLC purification, [18F]FBz-DBCO was reacted with the modified peptide and the putative radiotracer purified by HPLC. In vivo imaging using the radiolabeled amine was performed in mice bearing either TG2 expressing MDA-MB-231 or non-TG2 expressing MCF-7 xenografts as negative control. Expression of the target was confirmed using immunohistochemistry and western blot techniques. Results: We obtained 9 ± 2 GBq of the radiolabeled peptide from 55 ± 5 GBq of fluorine-18 in an overall synthesis time of 160 min from end of bombardment (EOB), including HPLC purification and reformulation. Small animal PET/MR imaging showed that visualization of MDA-MB-231 tumors using the radiolabeled peptide could only be achieved due to differences in clearance between tumor and surrounding tissue. In the MCF-7 xenograft model, radiotracer clearance from tumor and surrounding tissue occurred at a similar rate, thus making it impossible to visualize MCF-7 tumors. The presence of TG2 in MDA-MB-231 tumors and absence in MCF-7 tumors was confirmed by immunohistochemistry staining and western blot analysis. Conclusion: A fully automated synthesis of a TG2 selective, 13-amino-acid peptide modified with 5-azido pentynoic acid at the N-terminal was established using [18F]FBzDBCO as a prosthetic group. Although our results show that radiolabeled peptides have potential as imaging agents for TG2, more research needs to be performed to improve radiotracer kinetics.
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