Why does phosphodiester bond have diester as part of it's name?

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Discussion Overview

The discussion revolves around the nomenclature of the "phosphodiester bond," specifically why "diester" is included in its name. Participants explore the chemical structure and bonding involved in phosphodiester bonds, including references to esters and the role of ribose and phosphate groups.

Discussion Character

  • Conceptual clarification
  • Technical explanation
  • Debate/contested

Main Points Raised

  • One participant questions the inclusion of "diester" in the term, noting a lack of clarity regarding the presence of two esters.
  • Another participant references Wikipedia, stating that a phosphodiester bond consists of strong covalent bonds between a phosphate group and two pentoses, involving two ester bonds.
  • It is suggested that the term "diester" may relate to the presence of two C-O-P bonds, contrasting with the typical C-O-C bond found in standard esters.
  • A participant expresses confusion regarding the distinction between phosphodiester bonds and ethers.
  • Further clarification is provided that "ester" is a general term for products derived from the condensation of an acid and an alcohol, which may apply to inorganic oxo acids like phosphoric acid.

Areas of Agreement / Disagreement

Participants express differing views on the nomenclature and structure of phosphodiester bonds, with no consensus reached on the reasons behind the term "diester." The discussion remains unresolved regarding the clarity of the term's application.

Contextual Notes

Participants highlight potential confusion regarding the definitions of esters and their application to phosphodiester bonds, as well as the structural characteristics of the involved chemical groups.

gauss44
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Why does "phosphodiester bond" have "diester" as part of it's name?

Why does "phosphodiester bond" have "diester" as part of it's name?

I don't see two esters. I must be overlooking something. Maybe it's because the two riboses can dissociate into ester form? Thanks.
 
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Probably because it contains two C-O-P bonds (a normal ester is a C-O-C bond [where one of the carbons is a carbonyl], so a singel phosphoester would be a C-O-P bond [in which the phosphorus atom is a phosphate]).
 
Ygggdrasil said:
Probably because it contains two C-O-P bonds (a normal ester is a C-O-C bond [where one of the carbons is a carbonyl], so a singel phosphoester would be a C-O-P bond [in which the phosphorus atom is a phosphate]).

I thought that was an ether.
 
jedishrfu said:
http://en.wikipedia.org/wiki/Phosphodiester_bond

A phosphodiester bond is a group of strong covalent bonds between a phosphate group and two 5-carbon ring carbohydrates (pentoses) over two ester bonds.

I'm still not seeing it. I see riboses and phosphate groups.
 
To quopte wikipedia:

Ester is a general term for the product derived from the condensation of an acid and an alcohol. Thus, the nomenclature extends to inorganic oxo acids, e.g. phosphoric acid, sulfuric acid, nitric acid and boric acid.

(bolding mine)
 

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