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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: 759* 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
MLA 8th Edition
Jerić, Ivanka, et al. "Synthesis of Trehalose-centered Dipeptide Esters." Croatica Chemica Acta, vol. 79, no. 2, 2006, pp. 261-272. Accessed 11 Jul. 2020.
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.
Jerić, I., et al. (2006). 'Synthesis of Trehalose-centered Dipeptide Esters', Croatica Chemica Acta, 79(2), pp. 261-272. Available at: (Accessed 11 July 2020)
Jerić I, Momčilović M, Bratoš I, Horvat Š. Synthesis of Trehalose-centered Dipeptide Esters. Croatica Chemica Acta [Internet]. 2006 [cited 2020 July 11];79(2):261-272. Available from:
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: [Accessed: 11 July 2020]

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.

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

Hrčak ID: 4157


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