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Literature DB >> 22394273

An asymmetric synthesis of L-pyrrolysine.

Margaret L Wong¹, Ilia A Guzei, Laura L Kiessling.

Abstract

An efficient asymmetric synthesis of the 22nd amino acid L-pyrrolysine has been accomplished. The key stereogenic centers were installed by an asymmetric conjugate addition reaction. A Staudinger/aza-Wittig cyclization was used to form the acid-sensitive pyrroline ring. Pyrrolysine was synthesized in 13 steps in 20% overall yield.

Entities: Chemical Disease Species

Mesh：

Substances：
pyrrolysine
Lysine

Year: 2012 PMID： 22394273 PMCID： PMC3326344 DOI： 10.1021/ol300045c

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

27 in total

1. Flow synthesis of organic azides and the multistep synthesis of imines and amines using a new monolithic triphenylphosphine reagent.

Authors: Catherine J Smith; Christopher D Smith; Nikzad Nikbin; Steven V Ley; Ian R Baxendale
Journal: Org Biomol Chem Date: 2011-01-31 Impact factor: 3.876

2. A natural genetic code expansion cassette enables transmissible biosynthesis and genetic encoding of pyrrolysine.

Authors: David G Longstaff; Ross C Larue; Joseph E Faust; Anirban Mahapatra; Liwen Zhang; Kari B Green-Church; Joseph A Krzycki
Journal: Proc Natl Acad Sci U S A Date: 2007-01-04 Impact factor: 11.205

3. A pyrrolysine analogue for site-specific protein ubiquitination.

Authors: Xin Li; Tomasz Fekner; Jennifer J Ottesen; Michael K Chan
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

4. Genetically encoded 1,2-aminothiols facilitate rapid and site-specific protein labeling via a bio-orthogonal cyanobenzothiazole condensation.

Authors: Duy P Nguyen; Thomas Elliott; Matthew Holt; Tom W Muir; Jason W Chin
Journal: J Am Chem Soc Date: 2011-07-07 Impact factor: 15.419

Review 5. Biological chemistry of naturally occurring thiols of microbial and marine origin.

Authors: Christine E Hand; John F Honek
Journal: J Nat Prod Date: 2005-02 Impact factor: 4.050

6. Pyrrolysine encoded by UAG in Archaea: charging of a UAG-decoding specialized tRNA.

Authors: Gayathri Srinivasan; Carey M James; Joseph A Krzycki
Journal: Science Date: 2002-05-24 Impact factor: 47.728

7. Direct charging of tRNA(CUA) with pyrrolysine in vitro and in vivo.

Authors: Sherry K Blight; Ross C Larue; Anirban Mahapatra; David G Longstaff; Edward Chang; Gang Zhao; Patrick T Kang; Kari B Green-Church; Michael K Chan; Joseph A Krzycki
Journal: Nature Date: 2004-08-25 Impact factor: 49.962

8. Recognition of non-alpha-amino substrates by pyrrolysyl-tRNA synthetase.

Authors: Takatsugu Kobayashi; Tatsuo Yanagisawa; Kensaku Sakamoto; Shigeyuki Yokoyama
Journal: J Mol Biol Date: 2008-12-11 Impact factor: 5.469

9. Calcium-catalyzed diastereo- and enantioselective 1,4-addition of glycine derivatives to alpha,beta-unsaturated esters.

Authors: Shū Kobayashi; Tetsu Tsubogo; Susumu Saito; Yasuhiro Yamashita
Journal: Org Lett Date: 2008-01-29 Impact factor: 6.005

Review 7. Access to any site directed stable isotope ((2)H, (13)C, (15)N, (17)O and (18)O) in genetically encoded amino acids.

Authors: Prativa B S Dawadi; Johan Lugtenburg
Journal: Molecules Date: 2013-01-02 Impact factor: 4.411

7 in total

An asymmetric synthesis of L-pyrrolysine.

1. Flow synthesis of organic azides and the multistep synthesis of imines and amines using a new monolithic triphenylphosphine reagent.

2. A natural genetic code expansion cassette enables transmissible biosynthesis and genetic encoding of pyrrolysine.

3. A pyrrolysine analogue for site-specific protein ubiquitination.

4. Genetically encoded 1,2-aminothiols facilitate rapid and site-specific protein labeling via a bio-orthogonal cyanobenzothiazole condensation.

Review 5. Biological chemistry of naturally occurring thiols of microbial and marine origin.

6. Pyrrolysine encoded by UAG in Archaea: charging of a UAG-decoding specialized tRNA.

7. Direct charging of tRNA(CUA) with pyrrolysine in vitro and in vivo.

8. Recognition of non-alpha-amino substrates by pyrrolysyl-tRNA synthetase.

9. Calcium-catalyzed diastereo- and enantioselective 1,4-addition of glycine derivatives to alpha,beta-unsaturated esters.

10. A pyrrolysine analogue for protein click chemistry.

Review 1. Pyrrolysyl-tRNA synthetase: an ordinary enzyme but an outstanding genetic code expansion tool.

2. Polyspecific pyrrolysyl-tRNA synthetases from directed evolution.

3. Pyrrolysyl-tRNA synthetase, an aminoacyl-tRNA synthetase for genetic code expansion.

4. Crystal structures reveal an elusive functional domain of pyrrolysyl-tRNA synthetase.

5. Continuous directed evolution of aminoacyl-tRNA synthetases.

6. Improved pyrrolysine biosynthesis through phage assisted non-continuous directed evolution of the complete pathway.

Review 7. Access to any site directed stable isotope ((2)H, (13)C, (15)N, (17)O and (18)O) in genetically encoded amino acids.