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Poc-O2Oc-OH*DCHA
Chemical name: 8-(Popargylyloxycarbonyl-amino)-3,6-dioxaoctanoic acid dicyclohexylamine // Synonyms: {2-[2-(Poc-amino)ethoxy]ethoxy}acetic acid, 10-oxo-3,6,11-trioxa-9-azatetradec-13-yn-1-oic acid, 2-[2-(-{[(prop-2-yn-1-yloxy)carbonyl]amino}ethoxy)ethoxy]acetic acid,(propargyloxy)carbonyl-AEEA, Poc -AEEA, Pryoc-AEEA dicyclohexylamine salt
- Product code:PAA1050
- CAS No.:2988660-57-5
- Formula:C10H15NO6*C12H23N
- Storage temperature:-20°C
- Molecular weight:245.23*181.32 g/mol
- Purity :min. 98%
from $135.00
description
PEGylating spacer molecule suitable for standard Click conjugation. In combination with tetrazine linkers it can also be used in copper-free Click conjugations (Diels-Alderreactions).
Propargyloxycarbonyl, commonly abbreviated as Poc or Pryoc, can either be used as alkyne component for standard Click conjugation or in combination withtetrazine linkers in copper-free Diels-Alder type Click reactions. It also has applications as unusual protecting group for amines, hydroxy functions and as esters. All 3 are stable to neat TFA, but can be cleaved at ambient temperature with Co2(CO)8 in TFA:DCM. Deprotection with other transition metals like palladium have also been reported.
references
N-alkynyl derivatives of 5-fluorouracil: susceptibility to palladium-mediated dealkylation and toxigenicity in cancer cell culture; Jason T. Weiss, Craig Fraser, Belén Rubio-Ruiz, Samuel H. Myers, Richard Crispin, John C. Dawson, Valerie G. Brunton, E. Elizabeth Patton, Neil O. Carragher and Asier Unciti-Broceta; Frontiers in Chemistry 2014; 2(56): 1-9. doi: 10.3389/fchem.2014.00056.
Bioorthogonal Catalysis: A General Method To Evaluate Metal-Catalyzed Reactions in Real Time in Living Systems Using a Cellular Luciferase Reporter System; Hsiao-Tieh Hsu, Brian M. Trantow, Robert M. Waymouth, and Paul A. Wender; Bioconjugate Chem. 2015; DOI: 10.1021/acs.bioconjchem.5b00469.
Palladium-triggered deprotection chemistry for protein activation in living cells; Jie Li, Juntao Yu, Jingyi Zhao, Jie Wang, Siqi Zheng, Shixian Lin, Long Chen, Maiyun Yang, Shang Jia, Xiaoyu Zhang & Peng R. Chen; Nature Chemistry 2014; 6: 352-361. doi:10.1038/nchem.1887.
Propargyloxycarbonyl and propargyl groups for novel protection of amino, hydroxy, and carboxy functions; Yoshiyuki Fukase, Koichi Fukase, Shoichi Kusumoto; Tetrahedron Letters 1999; 40(6): 1169-1170. doi:10.1016/S0040-4039(98)02555-6.
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