The synthesis of allolactose from amygdalin

Davide Prosperi; Luigi Panza; Dietmar Haltrich; Micol Nonini; Sergio Riva

doi:10.1081/CAR-120023469

The synthesis of allolactose from amygdalin

Davide Prosperi, Luigi Panza, Dietmar Haltrich, Micol Nonini, Sergio Riva

Dipartimento di Scienze del Farmaco

Risultato della ricerca: Contributo su rivista › Articolo in rivista › peer review

Abstract

An original synthetic approach to the disaccharide allolactose (1) starting from the natural glycoside amygdalin (2) has been developed. The disaccharidic gentiobiose unit present in 2 has been transformed into the allolactose moiety using a four step protocol based on the selective inversion of the C-4′ OH. The efficient removal of the natural benzylic aglycone (a mandelonitrile moiety) was accomplished by catalytic transfer hydrogenolysis. The behavior of allolactose with different enzymes is also described.

Lingua originale	Inglese
pagine (da-a)	267-274
Numero di pagine	8
Rivista	Journal of Carbohydrate Chemistry
Volume	22
Numero di pubblicazione	5
DOI	https://doi.org/10.1081/CAR-120023469
Stato di pubblicazione	Pubblicato - 2003

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10.1081/CAR-120023469

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title = "The synthesis of allolactose from amygdalin",

abstract = "An original synthetic approach to the disaccharide allolactose (1) starting from the natural glycoside amygdalin (2) has been developed. The disaccharidic gentiobiose unit present in 2 has been transformed into the allolactose moiety using a four step protocol based on the selective inversion of the C-4′ OH. The efficient removal of the natural benzylic aglycone (a mandelonitrile moiety) was accomplished by catalytic transfer hydrogenolysis. The behavior of allolactose with different enzymes is also described.",

keywords = "Allolactose, Amygdalin, Analytical standard, Oxidoreductases",

author = "Davide Prosperi and Luigi Panza and Dietmar Haltrich and Micol Nonini and Sergio Riva",

note = "Funding Information: This work was supported by an European Commission grant (FAIR CT96-1048).",

year = "2003",

doi = "10.1081/CAR-120023469",

language = "English",

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journal = "Journal of Carbohydrate Chemistry",

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T1 - The synthesis of allolactose from amygdalin

AU - Prosperi, Davide

AU - Panza, Luigi

AU - Haltrich, Dietmar

AU - Nonini, Micol

AU - Riva, Sergio

N1 - Funding Information: This work was supported by an European Commission grant (FAIR CT96-1048).

PY - 2003

Y1 - 2003

N2 - An original synthetic approach to the disaccharide allolactose (1) starting from the natural glycoside amygdalin (2) has been developed. The disaccharidic gentiobiose unit present in 2 has been transformed into the allolactose moiety using a four step protocol based on the selective inversion of the C-4′ OH. The efficient removal of the natural benzylic aglycone (a mandelonitrile moiety) was accomplished by catalytic transfer hydrogenolysis. The behavior of allolactose with different enzymes is also described.

AB - An original synthetic approach to the disaccharide allolactose (1) starting from the natural glycoside amygdalin (2) has been developed. The disaccharidic gentiobiose unit present in 2 has been transformed into the allolactose moiety using a four step protocol based on the selective inversion of the C-4′ OH. The efficient removal of the natural benzylic aglycone (a mandelonitrile moiety) was accomplished by catalytic transfer hydrogenolysis. The behavior of allolactose with different enzymes is also described.

KW - Allolactose

KW - Amygdalin

KW - Analytical standard

KW - Oxidoreductases

UR - https://www.scopus.com/pages/publications/0042071284

U2 - 10.1081/CAR-120023469

DO - 10.1081/CAR-120023469

M3 - Article

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VL - 22

SP - 267

EP - 274

JO - Journal of Carbohydrate Chemistry

JF - Journal of Carbohydrate Chemistry

IS - 5

ER -

The synthesis of allolactose from amygdalin

Abstract

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