Facile Synthetic Route to Ascorbic Acid-Dipeptide Conjugate via N-Terminal Activation of Peptide on Resin Support
- Title
- Facile Synthetic Route to Ascorbic Acid-Dipeptide Conjugate via N-Terminal Activation of Peptide on Resin Support
- Author
- 김종호
- Keywords
- Carbamate formation; Ascorbic acid; Peptide conjugate; Antioxidant; Solid-phase synthesis
- Issue Date
- 2014-08
- Publisher
- 대한화학회
- Citation
- Bulletin of the Korean Chemical Society, v. 35, NO. 8, Page. 2381-2384
- Abstract
- 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 degrees C. As-prepared ASA-dipeptide conjugate (ASA-Ala-Ala) showed improved antioxidant activity compared to ASA.
- URI
- http://koreascience.or.kr/article/JAKO201423261321722.pagehttps://repository.hanyang.ac.kr/handle/20.500.11754/175967
- ISSN
- 0253-2964;1229-5949
- DOI
- 10.5012/bkcs.2014.35.8.2381
- Appears in Collections:
- COLLEGE OF ENGINEERING SCIENCES[E](공학대학) > MATERIALS SCIENCE AND CHEMICAL ENGINEERING(재료화학공학과) > Articles
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