A convenient procedure for the solid-phase synthesis of hydroxamic acids on PEGA resins
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A convenient procedure for the solid-phase synthesis of hydroxamic acids on PEGA resins. / Nandurkar, Nitin S.; Petersen, Rico; Qvortrup, Katrine; Komnatnyy, Vitaly V.; Taveras, Kennedy M.; Le Quement, Sebastian T.; Frauenlob, Robin; Givskov, Michael; Nielsen, Thomas E.
In: Tetrahedron Letters, Vol. 52, No. 52, 28.12.2011, p. 7121-7124.Research output: Contribution to journal › Journal article › Research › peer-review
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TY - JOUR
T1 - A convenient procedure for the solid-phase synthesis of hydroxamic acids on PEGA resins
AU - Nandurkar, Nitin S.
AU - Petersen, Rico
AU - Qvortrup, Katrine
AU - Komnatnyy, Vitaly V.
AU - Taveras, Kennedy M.
AU - Le Quement, Sebastian T.
AU - Frauenlob, Robin
AU - Givskov, Michael
AU - Nielsen, Thomas E.
N1 - Funding Information: The Hans Christian Oersted Postdoc Program, Technical University of Denmark (DTU), Carlsberg Foundation, Lundbeck Foundation, Danish Councils for Strategic and Independent Research, and Holm Foundation are gratefully acknowledged for the financial support.
PY - 2011/12/28
Y1 - 2011/12/28
N2 - An efficient method for the solid-phase synthesis of hydroxamic acids is described. The method comprises the nucleophilic displacement of esters immobilized on PEGA resins with hydroxylamine/sodium hydroxide in isopropanol. The hydroxyaminolysis protocol is compatible with a broad range of PEGA-supported peptide and peptidomimetic esters. The methodology was found to be compatible with two new strategies for the synthesis of solid-supported lactams and diketopiperazines, respectively, both relying on the high inter- and intramolecular reactivity of cyclic N-acyliminium ions with electron-rich aromatics and heteroaromatics, ultimately affording hydroxamic acid derivatives in high purities.
AB - An efficient method for the solid-phase synthesis of hydroxamic acids is described. The method comprises the nucleophilic displacement of esters immobilized on PEGA resins with hydroxylamine/sodium hydroxide in isopropanol. The hydroxyaminolysis protocol is compatible with a broad range of PEGA-supported peptide and peptidomimetic esters. The methodology was found to be compatible with two new strategies for the synthesis of solid-supported lactams and diketopiperazines, respectively, both relying on the high inter- and intramolecular reactivity of cyclic N-acyliminium ions with electron-rich aromatics and heteroaromatics, ultimately affording hydroxamic acid derivatives in high purities.
KW - HDAC inhibitor
KW - Hydroxamic acids
KW - Hydroxylamine
KW - PEGA resin
KW - Solid-phase synthesis
UR - http://www.scopus.com/inward/record.url?scp=82255193897&partnerID=8YFLogxK
U2 - 10.1016/j.tetlet.2011.10.103
DO - 10.1016/j.tetlet.2011.10.103
M3 - Journal article
AN - SCOPUS:82255193897
VL - 52
SP - 7121
EP - 7124
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 52
ER -
ID: 340024015