O-Propargyl-Puromycin

• CAT Number: I013533
• CAS Number: 1416561-90-4
• Molecular Formula: C₂₄H₂₉N₇O₅
• Molecular Weight: 495.53
• Purity: ≥95%
• Target: Alkynes
• Solubility: DMSO: ≥ 31 mg/mL; in vivo: dissolved in DMSO and then dilluted with PBS (final DMSO concertration is 10%).
• IUPAC Name: (2S)-2-amino-N-[(2S,3S,4R,5R)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-(4-prop-2-ynoxyphenyl)propanamide
• InChI: InChI=1S/C24H29N7O5/c1-4-9-35-15-7-5-14(6-8-15)10-16(25)23(34)29-18-17(11-32)36-24(20(18)33)31-13-28-19-21(30(2)3)26-12-27-22(19)31/h1,5-8,12-13,16-18,20,24,32-33H,9-11,25H2,2-3H3,(H,29,34)/t16-,17+,18+,20+,24+/m0/s1
• InChIKey: JXBIGWQNNSJLQK-IYRMOJGWSA-N
• SMILES: CN(C)C1=NC=NC2=C1N=CN2C3C(C(C(O3)CO)NC(=O)C(CC4=CC=C(C=C4)OCC#C)N)O

O-propargyl-puromycin (CAT: I013533) is an alkyne analog of puromycin, a well-known protein synthesis inhibitor. It acts by prematurely terminating protein translation during the process of elongation. O-propargyl-puromycin, due to the presence of an alkyne group, allows for the incorporation of specific tags or labels into newly synthesized proteins through click chemistry or bioorthogonal labeling techniques. This feature makes O-propargyl-puromycin a valuable tool in protein synthesis studies, as it enables the visualization and tracking of nascent proteins in various biological systems.

Reference

1. Proc Natl Acad Sci U S A. 2012 Jan 10;109(2):413-8. doi: 10.1073/pnas.1111561108. Epub 2011 Dec 12.
Imaging protein synthesis in cells and tissues with an alkyne analog of puromycin.
Liu J(1), Xu Y, Stoleru D, Salic A.
Author information:
(1)Department of Cell Biology, Harvard Medical School, 240 Longwood Avenue, Boston, MA 02115, USA.
Synthesis of many proteins is tightly controlled at the level of translation, and plays an essential role in fundamental processes such as cell growth and proliferation, signaling, differentiation, or death. Methods that allow imaging and identification of nascent proteins are critical for dissecting regulation of translation, both spatially and temporally, particularly in whole organisms. We introduce a simple and robust chemical method to image and affinity-purify nascent proteins in cells and in animals, based on an alkyne analog of puromycin, O-propargyl-puromycin (OP-puro). OP-puro forms covalent conjugates with nascent polypeptide chains, which are rapidly turned over by the proteasome and can be visualized or captured by copper(I)-catalyzed azide-alkyne cycloaddition. Unlike methionine analogs, OP-puro does not require methionine-free conditions and, uniquely, can be used to label and assay nascent proteins in whole organisms. This strategy should have broad applicability for imaging protein synthesis and for identifying proteins synthesized under various physiological and pathological conditions in vivo.