H-L-Phe(4-NH-Poc)-OH*HCl

Chemical name: 4-(Propargyloxycarbonyl)amino-L-phenylalanine hydrochloride // Synonyms: H-Phe(4-NH-Poc)*HCl, H-L-Aph(Poc)-OH*HCl, H-4Aph(Poc)*HCl, H-L-4Aph(Poc)-OH*HCl, H-L-4-Aph(Poc)-OH*HCl, H-p-amino-Phe(Poc)-OH*HCl, H-L-Phe(4-NH-Pryoc)-OH*HCl, H-4Aph(Pryoc)*HCl, H-L-4Aph(Pryoc)-OH*HCl, H-L-4-Aph(Pryoc)-OH*HCl, H-p-amino-Phe(Pryoc)-OH*HCl, (1S)-1-carboxy-2-(4-{[(prop-2-yn-1-yloxy)carbonyl]amino}phenyl)ethan-1-aminium hydrochloride

Product code:HAA4970
Formula:C13H14N2O4*HCl
Molecular weight:262,26*36,45 g/mol
Grouped product items
Qty Packing unit Price SKU
250 mg
$108.00
HAA4970.0250
500 mg
$194.40
HAA4970.0500
1 g
$302.40
HAA4970.0001
5 g
$1,080.00
HAA4970.0005
25 g
$4,320.00
HAA4970.0025
description

Used as a modified Phe or Tyr analogue in protein and peptide biosynthesis. 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

Bioorthogonal Catalysis: A General Method To Evaluate Metal-Catalyzed Reactions in Real Time in Living Systems Using a Cellular Luciferase Reporter System; H. T. Hsu, B. M. Trantow, R. M. Waymouth and P. A. Wender; Bioconjug Chem 2016; 27: 376-82. https://doi.org/10.1021/acs.bioconjchem.5b00469

N-alkynyl derivatives of 5-fluorouracil: susceptibility to palladium-mediated dealkylation and toxigenicity in cancer cell culture; J. T. Weiss, C. Fraser, B. Rubio-Ruiz, S. H. Myers, R. Crispin, J. C. Dawson, V. G. Brunton, E. E. Patton, N. O. Carragher and A. Unciti-Broceta; Front Chem 2014; 2: 56. https://doi.org/10.3389/fchem.2014.00056

Palladium-triggered deprotection chemistry for protein activation in living cells; J. Li, J. Yu, J. Zhao, J. Wang, S. Zheng, S. Lin, L. Chen, M. Yang, S. Jia, X. Zhang and P. R. Chen; Nat Chem 2014; 6: 352-61. https://doi.org/10.1038/nchem.1887

Propargyloxycarbonyl and propargyl groups for novel protection of amino, hydroxy, and carboxy functions; Y. Fukase, K. Fukase and S. Kusumoto; Tetrahedron Letters 1999; 40: 1169-1170. https://doi.org/10.1016/s0040-4039(98)02555-6


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