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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 35, Number 8
BKCSDE 35(8)
August 20, 2014 

Facile Synthetic Route to Ascorbic Acid-Dipeptide Conjugate via N-Terminal Activation of Peptide on Resin Support
Jin-Kyoung Yang, Seon-Yeong Kwak, Su-Ji Jeon, Hye-In Kim, Jong-Ho Kim*, Yoon-Sik Lee*
Carbamate formation, Ascorbic acid, Peptide conjugate, Antioxidant, Solid-phase synthesis
A solid-phase synthetic approach is reported for the synthesis of an ascorbic acid (ASA)-dipeptide conjugate that exhibited enhanced antioxidant activity. The N-terminal amino group of dipeptide (Ala-Ala) on a resin support was first activated by 1,1'-carbonyldiimidazole (CDI), and then reacted with an ASA derivative. The addition of a base, triethylamine (TEA), promoted nucleophilic acylation of ASA derivative and yielded a desired product (ASA-Ala-Ala) with enhanced purity, when cleaved from the resin. Compared to the approach where a C3 hydroxyl group of ASA was first activated with CDI and then reacted with the amino group of dipeptide on the resin, this new approach allowed a significant reduction of a total reaction time from 120 h to 8 h at 25 oC. As-prepared ASA-dipeptide conjugate (ASA-Ala-Ala) showed improved antioxidant activity compared to ASA.
2381 - 2384
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