Easy chemo-enzymatic synthesis of human milk trisaccharides from a common selectively protected lactose building block

Article abstract of DOI:10.1080/07328300008544082

Three glycosyllactosides, contained in the neutral fraction of human milk oligosaccharides, were synthesised in a simple and straightforward manner through a sequence based on a chemo-enzymatic approach. Lipase catalysed regioselective 6'-O-acylation of benzyl β-lactoside, followed by the introduction of an isopropylidene group and acetylation afforded, depending on the reaction conditions, compounds 4a and 4b, which allow selective access to positions 3, 3' and 6'. Glycosylation with proper donors gave trisaccharides 6, 9 and 12.

Full text of DOI:10.1080/07328300008544082

This article was downloaded by: [North Dakota State University]
On: 19 October 2014, At: 12:29
Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number: 1072954
Registered office: Mortimer House, 37-41 Mortimer Street, London W1T 3JH, UK
Journal of Carbohydrate Chemistry
Publication details, including instructions for authors and
subscription information:
http://www.tandfonline.com/loi/lcar20
Easy Chemo-Enzymatic Synthesis
of Human Milk Trisaccharides from
a Common Selectively Protected
Lactose Building Block
Barbara La Ferla , Luigi Lay , Laura Poletti , Giovanni Russo &
Luigi Panza
a Università degli Studi di Milano, Dipartimento di Chimica
Organica e Industriale, Centro di Studio sulle Sostanze
Organiche Naturali del CNR , via G. Venezian, 21 20133
Milano, (Italy)
b Università degli Studi di Milano, Dipartimento di Chimica
Organica e Industriale, Centro di Studio sulle Sostanze
Organiche Naturali del CNR , via G. Venezian, 21 20133
Milano, (Italy)
c Università degli Studi di Milano, Dipartimento di Chimica
Organica e Industriale, Centro di Studio sulle Sostanze
Organiche Naturali del CNR , via G. Venezian, 21 20133
Milano, (Italy)
d Università degli Studi di Milano, Dipartimento di Chimica
Organica e Industriale, Centro di Studio sulle Sostanze
Organiche Naturali del CNR , via G. Venezian, 21 20133
Milano, (Italy)
e Università degli Studi del Piemonte Orientale, Facoltà di
Farmacia, Dipartimento di Scienze Mediche , Viale Ferrucci,
33 – 28100 Novara, (Italy)
Published online: 27 Feb 2008.
To cite this article: Barbara La Ferla , Luigi Lay , Laura Poletti , Giovanni Russo & Luigi
Panza (2000) Easy Chemo-Enzymatic Synthesis of Human Milk Trisaccharides from a Common
Selectively Protected Lactose Building Block, Journal of Carbohydrate Chemistry, 19:3,
331-343, DOI: 10.1080/07328300008544082
To link to this article: http://dx.doi.org/10.1080/07328300008544082

PLEASE SCROLL DOWN FOR ARTICLE
Taylor & Francis makes every effort to ensure the accuracy of all the information
(the “Content”) contained in the publications on our platform. However, Taylor
& Francis, our agents, and our licensors make no representations or warranties
whatsoever as to the accuracy, completeness, or suitability for any purpose of the
Content. Any opinions and views expressed in this publication are the opinions and
views of the authors, and are not the views of or endorsed by Taylor & Francis. The
accuracy of the Content should not be relied upon and should be independently
verified with primary sources of information. Taylor and Francis shall not be liable
for any losses, actions, claims, proceedings, demands, costs, expenses, damages,
and other liabilities whatsoever or howsoever caused arising directly or indirectly in
connection with, in relation to or arising out of the use of the Content.
This article may be used for research, teaching, and private study purposes. Any
substantial or systematic reproduction, redistribution, reselling, loan, sub-licensing,
systematic supply, or distribution in any form to anyone is expressly forbidden.
Terms & Conditions of access and use can be found at http://www.tandfonline.com/
page/terms-and-conditions