A Convergent Route to Enantiomers of the Bicyclic Monosaccharide Bradyrhizose Leads to Insight into the Bioactivity of an Immunologically Silent Lipopolysaccharide

Research output: Contribution to journal › Journal article › Research › peer-review

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A Convergent Route to Enantiomers of the Bicyclic Monosaccharide Bradyrhizose Leads to Insight into the Bioactivity of an Immunologically Silent Lipopolysaccharide. / Aboussafy, Claude Larriveé; Andersen Gersby, Lotte Bettina; Molinaro, Antonio; Newman, Mari Anne; Lowary, Todd L.

In: Journal of Organic Chemistry, Vol. 84, No. 1, 04.01.2019, p. 14-41.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Aboussafy, CL, Andersen Gersby, LB, Molinaro, A, Newman, MA & Lowary, TL 2019, 'A Convergent Route to Enantiomers of the Bicyclic Monosaccharide Bradyrhizose Leads to Insight into the Bioactivity of an Immunologically Silent Lipopolysaccharide', Journal of Organic Chemistry, vol. 84, no. 1, pp. 14-41. https://doi.org/10.1021/acs.joc.8b02206

APA

Aboussafy, C. L., Andersen Gersby, L. B., Molinaro, A., Newman, M. A., & Lowary, T. L. (2019). A Convergent Route to Enantiomers of the Bicyclic Monosaccharide Bradyrhizose Leads to Insight into the Bioactivity of an Immunologically Silent Lipopolysaccharide. Journal of Organic Chemistry, 84(1), 14-41. https://doi.org/10.1021/acs.joc.8b02206

Vancouver

Aboussafy CL, Andersen Gersby LB, Molinaro A, Newman MA, Lowary TL. A Convergent Route to Enantiomers of the Bicyclic Monosaccharide Bradyrhizose Leads to Insight into the Bioactivity of an Immunologically Silent Lipopolysaccharide. Journal of Organic Chemistry. 2019 Jan 4;84(1):14-41. https://doi.org/10.1021/acs.joc.8b02206

Author

Aboussafy, Claude Larriveé ; Andersen Gersby, Lotte Bettina ; Molinaro, Antonio ; Newman, Mari Anne ; Lowary, Todd L. / A Convergent Route to Enantiomers of the Bicyclic Monosaccharide Bradyrhizose Leads to Insight into the Bioactivity of an Immunologically Silent Lipopolysaccharide. In: Journal of Organic Chemistry. 2019 ; Vol. 84, No. 1. pp. 14-41.

Bibtex

@article{c525c622cb394851b06953a7163e04aa,
title = "A Convergent Route to Enantiomers of the Bicyclic Monosaccharide Bradyrhizose Leads to Insight into the Bioactivity of an Immunologically Silent Lipopolysaccharide",
abstract = "The synthesis of bradyrhizose, the monosaccharide component of the lipopolysaccharide O-antigen of the nitrogen-fixing bacteria Bradyrhizobium sp. BTAi1 and sp. ORS278, has been achieved in 25 steps in an overall yield of 6% using myo-inositol and ethyl propiolate as the starting materials. The route involved the late-stage resolution of a racemic intermediate to provide both enantiomers of this unusual bicyclic monosaccharide. Both the natural d-enantiomer, and the unnatural and heretofore unknown l-enantiomer, were converted to disaccharide derivatives containing different forms of the monosaccharide (d,d; l,l; d,l; l,d). Evaluation of the synthetic compounds for their ability to act as microbe-associated molecular patterns in plants, through induction of reactive oxygen species, was investigated. These experiments suggest that the immunologically silent nature of the natural glycans is due to specific structural features.",
author = "Aboussafy, {Claude Larrive{\'e}} and {Andersen Gersby}, {Lotte Bettina} and Antonio Molinaro and Newman, {Mari Anne} and Lowary, {Todd L.}",
year = "2019",
month = jan,
day = "4",
doi = "10.1021/acs.joc.8b02206",
language = "English",
volume = "84",
pages = "14--41",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "1",

}

RIS

TY - JOUR

T1 - A Convergent Route to Enantiomers of the Bicyclic Monosaccharide Bradyrhizose Leads to Insight into the Bioactivity of an Immunologically Silent Lipopolysaccharide

AU - Aboussafy, Claude Larriveé

AU - Andersen Gersby, Lotte Bettina

AU - Molinaro, Antonio

AU - Newman, Mari Anne

AU - Lowary, Todd L.

PY - 2019/1/4

Y1 - 2019/1/4

N2 - The synthesis of bradyrhizose, the monosaccharide component of the lipopolysaccharide O-antigen of the nitrogen-fixing bacteria Bradyrhizobium sp. BTAi1 and sp. ORS278, has been achieved in 25 steps in an overall yield of 6% using myo-inositol and ethyl propiolate as the starting materials. The route involved the late-stage resolution of a racemic intermediate to provide both enantiomers of this unusual bicyclic monosaccharide. Both the natural d-enantiomer, and the unnatural and heretofore unknown l-enantiomer, were converted to disaccharide derivatives containing different forms of the monosaccharide (d,d; l,l; d,l; l,d). Evaluation of the synthetic compounds for their ability to act as microbe-associated molecular patterns in plants, through induction of reactive oxygen species, was investigated. These experiments suggest that the immunologically silent nature of the natural glycans is due to specific structural features.

AB - The synthesis of bradyrhizose, the monosaccharide component of the lipopolysaccharide O-antigen of the nitrogen-fixing bacteria Bradyrhizobium sp. BTAi1 and sp. ORS278, has been achieved in 25 steps in an overall yield of 6% using myo-inositol and ethyl propiolate as the starting materials. The route involved the late-stage resolution of a racemic intermediate to provide both enantiomers of this unusual bicyclic monosaccharide. Both the natural d-enantiomer, and the unnatural and heretofore unknown l-enantiomer, were converted to disaccharide derivatives containing different forms of the monosaccharide (d,d; l,l; d,l; l,d). Evaluation of the synthetic compounds for their ability to act as microbe-associated molecular patterns in plants, through induction of reactive oxygen species, was investigated. These experiments suggest that the immunologically silent nature of the natural glycans is due to specific structural features.

UR - http://www.scopus.com/inward/record.url?scp=85059584152&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.8b02206

DO - 10.1021/acs.joc.8b02206

M3 - Journal article

C2 - 30525636

AN - SCOPUS:85059584152

VL - 84

SP - 14

EP - 41

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 1

ER -

ID: 216210686