Boc-L-Phe(4-NH-Poc)-OH

Chemical name: N-alpha-t-Butyloxycarbonyl-4-(propargyloxycarbonyl)amino-L-phenylalanine // Synonyms: Boc-Phe(4-NH-Poc), Boc-L-Aph(Poc)-OH, Boc-4Aph(Poc), Boc-L-4Aph(Poc)-OH, Boc-L-4-Aph(Poc)-OH, Boc-p-amino-Phe(Poc)-OH, Boc-L-Phe(4-NH-Poc)-OH, Boc-4Aph(Pryoc), Boc-L-4Aph(Pryoc)-OH, Boc-L-4-Aph(Pryoc)-OH, Boc-p-amino-Phe(Pryoc)-OH, (2S)‐2‐{[(tert‐butoxy)carbonyl]amino}‐3‐(4‐{[(prop‐2‐yn‐1‐yloxy)carbonyl]amino}phenyl)propanoic acid

Art-No.:BAA3980
Formula:C18H22N2O6
Molecular weight:362,38 g/mol
Grouped product items
Product variant
500 mg
$170.10
BAA3980.0500
1 g
$264.60
BAA3980.0001
5 g
$945.00
BAA3980.0005
25 g
$3,780.00
BAA3980.0025
description
Used as an orthogonally protected building block in peptide synthesis. Propargyloxycarbonyl, commonly abbreviated as Poc or Pryoc, can either be used as alkyne component for standard Click conjugation or in combination with tetrazine 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, Beln 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. 2016; 27(2): 376-382. 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 Zha ng & 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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