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Synthesis of Trehalose-centered Dipeptide Esters

Ivanka Jerić
Marko Momčilović
Igor Bratoš
Štefica Horvat

Puni tekst: engleski, pdf (378 KB) str. 261-272 preuzimanja: 822* citiraj
APA 6th Edition
Jerić, I., Momčilović, M., Bratoš, I. i Horvat, Š. (2006). Synthesis of Trehalose-centered Dipeptide Esters. Croatica Chemica Acta, 79 (2), 261-272. Preuzeto s
MLA 8th Edition
Jerić, Ivanka, et al. "Synthesis of Trehalose-centered Dipeptide Esters." Croatica Chemica Acta, vol. 79, br. 2, 2006, str. 261-272. Citirano 26.10.2021.
Chicago 17th Edition
Jerić, Ivanka, Marko Momčilović, Igor Bratoš i Štefica Horvat. "Synthesis of Trehalose-centered Dipeptide Esters." Croatica Chemica Acta 79, br. 2 (2006): 261-272.
Jerić, I., et al. (2006). 'Synthesis of Trehalose-centered Dipeptide Esters', Croatica Chemica Acta, 79(2), str. 261-272. Preuzeto s: (Datum pristupa: 26.10.2021.)
Jerić I, Momčilović M, Bratoš I, Horvat Š. Synthesis of Trehalose-centered Dipeptide Esters. Croatica Chemica Acta [Internet]. 2006 [pristupljeno 26.10.2021.];79(2):261-272. Dostupno na:
I. Jerić, M. Momčilović, I. Bratoš i Š. Horvat, "Synthesis of Trehalose-centered Dipeptide Esters", Croatica Chemica Acta, vol.79, br. 2, str. 261-272, 2006. [Online]. Dostupno na: [Citirano: 26.10.2021.]

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.

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

Hrčak ID: 4157


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