Cart
Article
A New Method To Convert the Fischer Projection of a Monosaccharide to the Haworth Projection
Hi-Res PDFPurchase the full-text
- PDF/HTML,
figures/images,
references and tables,
(where available)
Abstract
This method is based upon the R,S-configuration designation of each asymmetric carbon of a monosaccharide. According to the rule of configurational retention of each original asymmetric carbon, the Fischer projection of a monosaccharide can be converted into different views of the Haworth projection (the carbon-numbering orientation of the Haworth ring can be in either a clockwise or a counterclockwise direction, and the oxygen atom can be written at any corner of the ring). The d,l-configuration of a sugar in Haworth projection can be directly determined by designating the R,S-configuration of the highest-numbered asymmetric carbon; that is, the most distant carbon from the anomeric carbon. The R-configuration at this carbon corresponds to the d-family, and S- to the l-family. By comparing the stereochemistry of the anomeric carbon with that of the highest-numbered asymmetric carbon, the α,β-anomer of a Haworth projection is directly notated. If these two carbons have the same configuration (R,R or S,S), the anomer is β; if different (R,S or S,R), the anomer is α. This method proves to be general and widely applicable.
Keywords (Audience):
Second-Year UndergraduateKeywords (Domain):
Organic ChemistryKeywords (Subject):
CarbohydratesCiting Articles
Citation data is made available by participants in CrossRef's Cited-by Linking service. For a more comprehensive list of citations to this article, users are encouraged to perform a search in SciFinder.
This article has been cited by 4 ACS Journal articles (4 most recent appear below).
Understanding Fischer Projection and Angular Line Representation Conversion
Luis F. MorenoJournal of Chemical Education2012 89 (1), 175-176Understanding Fischer Projection and Angular Line Representation Conversion
Luis F. MorenoJournal of Chemical Education2012 89 (1), 175-176Difficulty for undergraduate students taking a basic organic chemistry course arises when they have to understand the relationship between the different molecular representations, for example, between Fischer and angular line representations. It is well ...
CARBOHYDECK: A Card Game To Teach the Stereochemistry of Carbohydrates
Manuel João CostaJournal of Chemical Education2007 84 (6), 977CARBOHYDECK: A Card Game To Teach the Stereochemistry of Carbohydrates
Manuel João CostaJournal of Chemical Education2007 84 (6), 977Identifying and differentiating monosaccharide isomers is an important educational goal in introductory biochemistry courses. However the topic is difficult for many students—in particular, chemistry nonmajors. This paper describes CARBOHYDECK, a card ...
The Use of Stick Figures to Visualize Fischer Projections
Laurie S. StarkeyJournal of Chemical Education2001 78 (11), 1486The Use of Stick Figures to Visualize Fischer Projections
Laurie S. StarkeyJournal of Chemical Education2001 78 (11), 1486This paper presents a very simple method for interconverting line drawings and Fischer projections. The technique uses stick figures to help students view these structures from the proper point of view.
Introducing Chiroscience into the Organic Laboratory Curriculum
Kenny B. Lipkowitz , Tim Naylor and Keith S. AnlikerJournal of Chemical Education2000 77 (3), 305Introducing Chiroscience into the Organic Laboratory Curriculum
Kenny B. Lipkowitz , Tim Naylor and Keith S. AnlikerJournal of Chemical Education2000 77 (3), 305Chirality transcends traditional boundaries separating subdisciplines of the chemical sciences. The large number of scientific studies focusing on the topic of chirality has now thrust it into the scientific forefront, especially in biological and organic ...
Full Text HTMLTools
-
Add to Favorites
-
Download Citation
-
Email a Colleague -
Permalink
Order Reprints
Rights & Permissions
Citation Alerts
History
- Received: August 03, 2009
ACS
Network
Facebook
Tweet This
CiteULike
Newsvine
Digg This
Delicious
