Photodecarboxylation of N-Adamantyl- and N-Phenylphthalimide Dipeptide Derivatives

Sohora, Margareta; Šumanovac Ramljak, Tatjana; Mlinarić-Majerski, Kata; Basarić, Nikola (2014) Photodecarboxylation of N-Adamantyl- and N-Phenylphthalimide Dipeptide Derivatives. Croatica chemica acta, 87 (4). pp. 431-446. ISSN 0011-1643

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Official URL: http://pubweb.carnet.hr/ccacaa/

Abstract

New dipeptide derivatives 1 and 3 were synthesized and their reactivity in the photochemical reaction of decarboxylation was investigated. The photodecarboxylation of N-adamantyl derivatives 1a and 1b and N-phenylphthalimide derivatives 3a and 3b probably takes place from the triplet excited state. The triplet excited state of 1a, 3a and 3b was characterized by laser flash photolysis. N-phenylphthalimides 3a and 3b undergo 2-5 times more efficient photodecarboxylation than N-adamantylphthalimides 1a and 1b. The aminoacid residue (Phe or Gly) at the C-terminus of the dipeptide does not influence the photodecarboxylation efficiency. Product selectivity in the photoreactions is determined by the conformation of the molecules. N-phenylphthalimides with the separated electron donor (carboxylate) and acceptor moiety (phthalimide) give only simple decarboxylation products, whereas N-adamantyl derivatives also give cyclization products.

Item Type:

Article

Uncontrolled Keywords:

Photodecarboxylation, Dipeptides, Phthalimides

Subjects:

NATURAL SCIENCES > Chemistry

Divisions:

Division of Organic Chemistry and Biochemistry

Projects:

Project title	Project leader	Project code	Project type
Fotokemija policikličkih molekula: od istraživanja mehanizama reakcije do novih lijekova i medicinskih primjena	[250000] Basarić Nikola	UIP-02.05/25	HRZZ
Kavezasti spojevi: ugradbene jedinice u molekularnim sustavima	[27342] Kata Majerski	098-0982933-2911	MZOS

Depositing User:

Sofija Konjević

Date Deposited:

10 Mar 2015 14:26

URI:

http://fulir.irb.hr/id/eprint/1713

DOI:

10.5562/cca2482