Threose is a four-carbon monosaccharide with molecular formula C4H8O4. It has a terminal aldehyde group rather than a ketone in its linear chain, and so is considered part of the aldose family of monosaccharides. The threose name can be used to refer to both the D- and L-stereoisomers, and more generally to the racemic mixture (D/L-, equal parts D- and L-) as well as to the more generic threose structure (absolute stereochemistry unspecified).
The prefix "threo" which derives from threose (and "erythro" from a corresponding diastereomererythrose) offer a useful way to describe general organic structures with adjacent chiral centers, where "the prefixes... designate the relative configuration of the centers".[3] As is depicted in a Fischer projection of D-threose, the adjacent substituents will have a syn orientation in the isomer referred to as "threo", and are anti in the isomer referred to as "erythro".[3][4]
^ abFormulas Using Other Configurational Notations, W. Rausch, accessed 1 March 2011
^Prof. Rausch helpfully notes that the prefixes "may be applied to racemic compounds, as well as pure enantiomers and meso compounds", and that when depicted in the common "zig-zag" representation, adjacent "substituents may lie on the same side of the carbon chain... [syn] or on opposite sides... [anti]", which is opposite of their depiction in a Fischer projection.
January 01, 1970
threose, four, carbon, monosaccharide, with, molecular, formula, c4h8o4, terminal, aldehyde, group, rather, than, ketone, linear, chain, considered, part, aldose, family, monosaccharides, threose, name, used, refer, both, stereoisomers, more, generally, racemi. Threose is a four carbon monosaccharide with molecular formula C4H8O4 It has a terminal aldehyde group rather than a ketone in its linear chain and so is considered part of the aldose family of monosaccharides The threose name can be used to refer to both the D and L stereoisomers and more generally to the racemic mixture D L equal parts D and L as well as to the more generic threose structure absolute stereochemistry unspecified Threose 1 D Threose L Threose Names IUPAC names D ThreoseL Threose 2 Systematic IUPAC name 2S 3R 2 3 4 Trihydroxybutanal D 2R 3S 2 3 4 Trihydroxybutanal L Other names Threotetrose Identifiers CAS Number 95 43 2 D Y95 44 3 L Y 3D model JSmol D Interactive image L Interactive image ChEBI CHEBI 28587 Y ChemSpider 388736 Y ECHA InfoCard 100 002 199 PubChem CID 439665 D UNII 4EHO9A06LX D YMHH79K1BVR L Y InChI InChI 1S C4H8O4 c5 1 3 7 4 8 2 6 h1 3 4 6 8H 2H2 t3 4 m1 s1 YKey YTBSYETUWUMLBZ QWWZWVQMSA N YInChI 1 C4H8O4 c5 1 3 7 4 8 2 6 h1 3 4 6 8H 2H2 t3 4 m1 s1Key YTBSYETUWUMLBZ QWWZWVQMBY SMILES D O C C H O C H O CO L OC C H O C H O C O Properties Chemical formula C 4H 8O 4 Molar mass 120 104 g mol 1 Appearance Syrup Solubility in water Very soluble Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references The prefix threo which derives from threose and erythro from a corresponding diastereomer erythrose offer a useful way to describe general organic structures with adjacent chiral centers where the prefixes designate the relative configuration of the centers 3 As is depicted in a Fischer projection of D threose the adjacent substituents will have a syn orientation in the isomer referred to as threo and are anti in the isomer referred to as erythro 3 4 Fischer projections depicting the two enantiomers of threoseSee also editThreitol Threonic acid Threose nucleic acidReferences edit Merck Index 11th Edition 9317 https iupac qmul ac uk 2carb a b Formulas Using Other Configurational Notations W Rausch accessed 1 March 2011 Prof Rausch helpfully notes that the prefixes may be applied to racemic compounds as well as pure enantiomers and meso compounds and that when depicted in the common zig zag representation adjacent substituents may lie on the same side of the carbon chain syn or on opposite sides anti which is opposite of their depiction in a Fischer projection Retrieved from https en wikipedia org w index php title Threose amp oldid 1175496611, wikipedia, wiki, book, books, library,
