Solid phase synthesis of hydrogen bond surrogate derived alpha-helices: resolving the case of a difficult amide coupling.
Solid phase synthesis of HBS helices involving the Fukuyama-Mitsunobu reaction and triphosgene coupling is described.
Patgiri
Anupam
A
Department of Chemistry, New York University, New York, NY 10003, USA.
Witten
Michael R
MR
Arora
Paramjit S
PS
D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry*; D006860:Hydrogen Bonding; D017433:Protein Structure, Secondary; D011506:Proteins / Q000138:chemical synthesis* / Q000737:chemistry
D000577:Amides; D011506:Proteins
J Am Chem Soc. 2010 Jan 27;132(3):941-3
20041650
Chem Soc Rev. 2007 Feb;36(2):326-34
17264933
Curr Opin Chem Biol. 2008 Dec;12(6):692-7
18793750
Org Lett. 2005 Jun 9;7(12):2389-92
15932205
J Pept Res. 1999 May;53(5):507-17
10424345
Org Biomol Chem. 2007 Nov 21;5(22):3577-85
17971985
Org Lett. 2006 Dec 7;8(25):5825-8
17134282
Angew Chem Int Ed Engl. 2008;47(10):1879-82
18224636
Org Lett. 2009 Sep 3;11(17):3910-3
19670849
Methods Enzymol. 1996;267:437-47
8743331
Angew Chem Int Ed Engl. 2005 Oct 14;44(40):6525-9
16172999
J Am Chem Soc. 2008 Apr 2;130(13):4334-7
18331030
Acc Chem Res. 2008 Oct;41(10):1289-300
18630933
Chem Commun (Camb). 2004 Feb 21;(4):353-9
14765207
J Am Chem Soc. 2004 Oct 6;126(39):12252-3
15453743
Angew Chem Int Ed Engl. 2002 Jul 2;41(13):2307-9
12203574