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Original scientific paper

Synthesis of Trehalose-centered Dipeptide Esters

Ivanka Jerić
Marko Momčilović
Igor Bratoš
Štefica Horvat

Fulltext: english, pdf (378 KB) pages 261-272 downloads: 739* cite
APA 6th Edition
Jerić, I., Momčilović, M., Bratoš, I. & Horvat, Š. (2006). Synthesis of Trehalose-centered Dipeptide Esters. Croatica Chemica Acta, 79 (2), 261-272. Retrieved from https://hrcak.srce.hr/4157
MLA 8th Edition
Jerić, Ivanka, et al. "Synthesis of Trehalose-centered Dipeptide Esters." Croatica Chemica Acta, vol. 79, no. 2, 2006, pp. 261-272. https://hrcak.srce.hr/4157. Accessed 24 Jul. 2019.
Chicago 17th Edition
Jerić, Ivanka, Marko Momčilović, Igor Bratoš and Štefica Horvat. "Synthesis of Trehalose-centered Dipeptide Esters." Croatica Chemica Acta 79, no. 2 (2006): 261-272. https://hrcak.srce.hr/4157
Harvard
Jerić, I., et al. (2006). 'Synthesis of Trehalose-centered Dipeptide Esters', Croatica Chemica Acta, 79(2), pp. 261-272. Available at: https://hrcak.srce.hr/4157 (Accessed 24 July 2019)
Vancouver
Jerić I, Momčilović M, Bratoš I, Horvat Š. Synthesis of Trehalose-centered Dipeptide Esters. Croatica Chemica Acta [Internet]. 2006 [cited 2019 July 24];79(2):261-272. Available from: https://hrcak.srce.hr/4157
IEEE
I. Jerić, M. Momčilović, I. Bratoš and Š. Horvat, "Synthesis of Trehalose-centered Dipeptide Esters", Croatica Chemica Acta, vol.79, no. 2, pp. 261-272, 2006. [Online]. Available: https://hrcak.srce.hr/4157. [Accessed: 24 July 2019]

Abstracts
Chemical esterification of α,α-trehalose with two different dipeptide acyl donors, Boc-Phe-Met-OH and Boc-Gly-Gly-OH, gave a set of products differing in the number and site of substitution. With both dipeptides 6,6'-diester was isolated as the major product. In the Boc-Phe-Met-OH line, the dipeptide units in all higher substituted esters were asymmetrically distributed between the two trehalose rings. In contrast, the first higher substituted Boc-Gly-Gly-OH derived ester found was the symmetric 2,2',6,6'-tetraester. These four sites remained occupied in all other isolated products, two asymmetric pentaesters and one symmetric hexaester. The data presented here show that in addition to sugar hydroxyl group reactivity, the structural properties of the acylating reagent, in particular its sterical demands, are of the utmost importance for the distribution and arrangement of acyl moieties around the non-reducing disaccharide core molecule.

Keywords
α,α-trehalose; chemical esterification; dipeptide; disaccharide esters

Hrčak ID: 4157

URI
https://hrcak.srce.hr/4157

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