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Synthesis of trehalose-centered dipeptide esters

Jerić, Ivanka; Momčilović, Marko; Bratoš, Igor; Horvat, Štefica (2006) Synthesis of trehalose-centered dipeptide esters. Croatica Chemica Acta, 79 (2). pp. 261-272. ISSN 0011-1643

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Chemical esterification of alpha,alpha-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.

Item Type: Article
Uncontrolled Keywords: alpha,alpha-trehalose; chemical esterification; dipeptide; disaccharide esters; protease-catalyzed synthesis; amino-acid esters; intramolecular reactions; peptide-synthesis; group migrations; sucrose; esterification; derivatives; reactivity; imidazole
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Division of Organic Chemistry and Biochemistry
Project titleProject leaderProject codeProject type
Dizajn i sinteza bioaktivnih peptida, glikopeptida i biomarkeraŠtefica Horvat0098054MZOS
Depositing User: Ivanka Jerić
Date Deposited: 29 Oct 2013 09:51

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