O-Propargyl-Puromycin

O-Propargyl-Puromycin, an alkyne analog of puromycin, is a potent protein synthesis inhibitor.

Product information

CAS Number: 1416561-90-4

Molecular Weight: 495.53

Formula: C24H29N7O5

Chemical Name: (2S)-2-amino-N-[(2S,3S,4R,5R)-5-[6-(dimethylamino)-9H-purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-[4-(prop-2-yn-1-yloxy)phenyl]propanamide

Smiles: CN(C)C1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](NC(=O)[C@@H](N)CC2C=CC(=CC=2)OCC#C)[C@H]1O

InChiKey: JXBIGWQNNSJLQK-IYRMOJGWSA-N

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

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: DMSO : ≥ 31 mg/mL (62.56 mM).

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

O-propargyl-puromycin can be used to image and affinity-purify nascent proteins in cells and in animals. O-propargyl-puromycin inhibits protein synthesis, both in reticulocyte lysates and in cultured cells, displaying a potency two- to threefold lower than that of unmodified puromycin. O-propargyl-puromycin 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. .

In Vivo:

Tissues from uninjected mice shows low nonspecific staining, whereas tissues from O-propargyl-puromycin-injected mice display specific patterns of O-propargyl-puromycin incorporation into nascent proteins. In the small intestine, translation is strongest in cells in the crypts and at the base of intestinal villi, consistent with the high proliferative and secretory activity of these cells. The stain is particularly strong in Paneth cells, which are located close to the base of the crypts and are filled with secretory vesicles. The intense O-propargyl-puromycin labeling of vesicles in Paneth cells suggests that prematurely terminated, O-propargyl-puromycin-conjugated secretory proteins are translocated into the endoplasmic reticulum (ER) lumen.

Products are for research use only. Not for human use.