<?xml version="1.0" encoding="UTF-8" standalone="yes"?><oembed><version><![CDATA[1.0]]></version><provider_name><![CDATA[amphoteros]]></provider_name><provider_url><![CDATA[http://amphoteros.com]]></provider_url><author_name><![CDATA[ayudin2013]]></author_name><author_url><![CDATA[https://amphoteros.com/author/ayudin2013/]]></author_url><title><![CDATA[Methylene taken away:&nbsp;norcysteine]]></title><type><![CDATA[link]]></type><html><![CDATA[<p>Today I want to talk about norcysteine, an unnatural analog of cysteine that has the methylene group &#8220;taken away&#8221;. That’s right.</p>
<p><a href="https://amphoteros.files.wordpress.com/2013/08/nor.jpg"><img class="size-full wp-image aligncenter" id="i-420" alt="Image" src="https://amphoteros.files.wordpress.com/2013/08/nor.jpg?w=487" srcset="https://amphoteros.files.wordpress.com/2013/08/nor.jpg?w=487 487w, https://amphoteros.files.wordpress.com/2013/08/nor.jpg?w=974 974w, https://amphoteros.files.wordpress.com/2013/08/nor.jpg?w=150 150w, https://amphoteros.files.wordpress.com/2013/08/nor.jpg?w=300 300w, https://amphoteros.files.wordpress.com/2013/08/nor.jpg?w=768 768w" sizes="(max-width: 487px) 100vw, 487px" /></a></p>
<p>You look at norcysteine and you go “How in the world is this stable?”. But apparently it is stable&#8230; Jean Rivier of the Salk Institute in La Jolla has done really nice work that demonstrates some of the unusual properties of this amino acid. Here is a representative paper:</p>
<p><a href="http://pubs.acs.org/doi/abs/10.1021/ol0606740" rel="nofollow">http://pubs.acs.org/doi/abs/10.1021/ol0606740</a></p>
<p>You might imagine that the corresponding SS bonds would be really different (shorter or longer SS bond?) from typical Cys-Cys connections. The thing for me is that the aldehyde oxidation state of the alpha-carbon might not mesh well with a reasonable expectation for configurational stability of this particular amino acid. However, norcysteine-containing peptides are configurationally stable at the alpha methine position. One can imagine a ton of applications for this molecule. I doubt we will see a variant of the native chemical ligation, but who knows?</p>
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