Liquidambar styraciflua: a renewable source of shikimic acid

Liza B. Enrich, Margaret L. Scheuermann, Ashley Mohadjer, Kathryn R Matthias, Chrystal F. Eller, M. Scott Newman, Michael Fujinaka, Thomas Poon

Research output: Contribution to journalArticle

42 Citations (Scopus)

Abstract

An isolation procedure is presented that yields 2.4-3.7% w/w pure shikimic acid from the seeds of Liquidambar styraciflua (Sweetgum). Shikimic acid, the starting material in the commercial synthesis of the antiviral agent oseltamivir and an important intermediate in the biosynthesis of aromatic amino acids in plants, was found by HPLC to be abundant in the granular, aborted seeds (6.5% w/w) while present only in small amounts in the developed, fertile seeds (0.14% w/w). This extraction technique makes L. styraciflua, which is found in 40 states of the continental US, a potential renewable source of this important natural product.

Original languageEnglish (US)
Pages (from-to)2503-2505
Number of pages3
JournalTetrahedron Letters
Volume49
Issue number16
DOIs
StatePublished - Apr 14 2008

Fingerprint

Liquidambar
Shikimic Acid
Seed
Seeds
Oseltamivir
Aromatic Amino Acids
Biosynthesis
Biological Products
Antiviral Agents
High Pressure Liquid Chromatography

Keywords

  • Liquidambar styraciflua
  • Plant natural products
  • Shikimic acid

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Enrich, L. B., Scheuermann, M. L., Mohadjer, A., Matthias, K. R., Eller, C. F., Newman, M. S., ... Poon, T. (2008). Liquidambar styraciflua: a renewable source of shikimic acid. Tetrahedron Letters, 49(16), 2503-2505. https://doi.org/10.1016/j.tetlet.2008.02.140

Liquidambar styraciflua : a renewable source of shikimic acid. / Enrich, Liza B.; Scheuermann, Margaret L.; Mohadjer, Ashley; Matthias, Kathryn R; Eller, Chrystal F.; Newman, M. Scott; Fujinaka, Michael; Poon, Thomas.

In: Tetrahedron Letters, Vol. 49, No. 16, 14.04.2008, p. 2503-2505.

Research output: Contribution to journalArticle

Enrich, LB, Scheuermann, ML, Mohadjer, A, Matthias, KR, Eller, CF, Newman, MS, Fujinaka, M & Poon, T 2008, 'Liquidambar styraciflua: a renewable source of shikimic acid', Tetrahedron Letters, vol. 49, no. 16, pp. 2503-2505. https://doi.org/10.1016/j.tetlet.2008.02.140
Enrich LB, Scheuermann ML, Mohadjer A, Matthias KR, Eller CF, Newman MS et al. Liquidambar styraciflua: a renewable source of shikimic acid. Tetrahedron Letters. 2008 Apr 14;49(16):2503-2505. https://doi.org/10.1016/j.tetlet.2008.02.140
Enrich, Liza B. ; Scheuermann, Margaret L. ; Mohadjer, Ashley ; Matthias, Kathryn R ; Eller, Chrystal F. ; Newman, M. Scott ; Fujinaka, Michael ; Poon, Thomas. / Liquidambar styraciflua : a renewable source of shikimic acid. In: Tetrahedron Letters. 2008 ; Vol. 49, No. 16. pp. 2503-2505.
@article{59fd74dee9d54cc28a57b8977526c1eb,
title = "Liquidambar styraciflua: a renewable source of shikimic acid",
abstract = "An isolation procedure is presented that yields 2.4-3.7{\%} w/w pure shikimic acid from the seeds of Liquidambar styraciflua (Sweetgum). Shikimic acid, the starting material in the commercial synthesis of the antiviral agent oseltamivir and an important intermediate in the biosynthesis of aromatic amino acids in plants, was found by HPLC to be abundant in the granular, aborted seeds (6.5{\%} w/w) while present only in small amounts in the developed, fertile seeds (0.14{\%} w/w). This extraction technique makes L. styraciflua, which is found in 40 states of the continental US, a potential renewable source of this important natural product.",
keywords = "Liquidambar styraciflua, Plant natural products, Shikimic acid",
author = "Enrich, {Liza B.} and Scheuermann, {Margaret L.} and Ashley Mohadjer and Matthias, {Kathryn R} and Eller, {Chrystal F.} and Newman, {M. Scott} and Michael Fujinaka and Thomas Poon",
year = "2008",
month = "4",
day = "14",
doi = "10.1016/j.tetlet.2008.02.140",
language = "English (US)",
volume = "49",
pages = "2503--2505",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "16",

}

TY - JOUR

T1 - Liquidambar styraciflua

T2 - a renewable source of shikimic acid

AU - Enrich, Liza B.

AU - Scheuermann, Margaret L.

AU - Mohadjer, Ashley

AU - Matthias, Kathryn R

AU - Eller, Chrystal F.

AU - Newman, M. Scott

AU - Fujinaka, Michael

AU - Poon, Thomas

PY - 2008/4/14

Y1 - 2008/4/14

N2 - An isolation procedure is presented that yields 2.4-3.7% w/w pure shikimic acid from the seeds of Liquidambar styraciflua (Sweetgum). Shikimic acid, the starting material in the commercial synthesis of the antiviral agent oseltamivir and an important intermediate in the biosynthesis of aromatic amino acids in plants, was found by HPLC to be abundant in the granular, aborted seeds (6.5% w/w) while present only in small amounts in the developed, fertile seeds (0.14% w/w). This extraction technique makes L. styraciflua, which is found in 40 states of the continental US, a potential renewable source of this important natural product.

AB - An isolation procedure is presented that yields 2.4-3.7% w/w pure shikimic acid from the seeds of Liquidambar styraciflua (Sweetgum). Shikimic acid, the starting material in the commercial synthesis of the antiviral agent oseltamivir and an important intermediate in the biosynthesis of aromatic amino acids in plants, was found by HPLC to be abundant in the granular, aborted seeds (6.5% w/w) while present only in small amounts in the developed, fertile seeds (0.14% w/w). This extraction technique makes L. styraciflua, which is found in 40 states of the continental US, a potential renewable source of this important natural product.

KW - Liquidambar styraciflua

KW - Plant natural products

KW - Shikimic acid

UR - http://www.scopus.com/inward/record.url?scp=40849104789&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=40849104789&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2008.02.140

DO - 10.1016/j.tetlet.2008.02.140

M3 - Article

AN - SCOPUS:40849104789

VL - 49

SP - 2503

EP - 2505

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 16

ER -