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Kamran Fateh

Why are nitrogenous bases of DNA hydrophobic if they can hydrogen bond?

Dimitra Tsiovolou  Follow

These two concepts are not mutually exclusive. You have constructed a false dichotomy. Both of these facts are true:

  1. The electrons in the pi orbitals of the conjugated double bonds in the planar rings are hydrophobic and can "stack" on each other as shown in this drawing of a DNA helix where the bases are shown as planar rectangles:

A model of a kinked DNA helix

  1. The nitrogen and oxygen molecules (either in the rings, or as substituents on the rings) can participate in hydrogen bonds (H-bonds):

H-bonds in Watson Crick base pairs

There are other examples of hydrophobicity and H-bonds co-existing. For example on the interior of proteins.

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Elena Elena  Follow
I am sorry, I don't understand the answer. Why are both the facts true? I think that is what I want to understand more.More
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Ed McManus  Follow
@Kendall Can you add that to the the answer?More
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Eli Pasternak  Follow
@Whitecat Most detergents are also hydrophobic and hydrophilic at the same time.More
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Halle Bloggs  Follow
I think the confusion here is that no, the DNA bases aren't in themselves completely hydrophobic, but in the region of the planar face of each base is a zone of hydrophobicity. In this way, base stacking becomes favorable where water molecules would otherwise attempt to order themselves to maximize hydrogen bonding with each other.More
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Eltrio2  Follow
Hydrophobicity and and hydrophilicity aren't yes/no things, they're gradients.More
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