Novel sulfur and selenium containing bis-alpha-amino acids from 4-hydroxyproline.

Amino Acids 2010 Jan 12;38(1):305-10. Epub 2009 Feb 12.

Dipartimento di Chimica Organica e Biochimica, Università di Napoli Federico II, 80126, Naples, Italy.

The synthesis of new substituted prolines carrying at C-4 a second alpha-amino acid residue is reported. The amino acid, L-cysteine or L-selenocysteine, is linked to the proline ring through the sulfur or the selenium atom, respectively. The products were prepared with different stereochemistry at C-4, in few and clean high-yielding steps, with suitable protections for solid phase applications. The introduction of both sulfur and selenium atoms at C-4 of the proline ring seems to enhance significantly the cis geometry at the prolyl amide bond.

Download full-text PDF

Source
http://dx.doi.org/10.1007/s00726-009-0251-xDOI Listing
January 2010

Publication Analysis

Top Keywords

sulfur selenium
12
proline ring
8
stereochemistry c-4
4
prepared stereochemistry
4
c-4 clean
4
clean high-yielding
4
steps suitable
4
high-yielding steps
4
products prepared
4
selenium atom
4
l-cysteine l-selenocysteine
4
acid l-cysteine
4
l-selenocysteine linked
4
linked proline
4
suitable protections
4
atom products
4
protections solid
4
enhance cis
4
ring enhance
4
cis geometry
4

Similar Publications