Literature DB >> 25504318

Myoglobin-catalyzed intermolecular carbene N-H insertion with arylamine substrates.

Gopeekrishnan Sreenilayam1, Rudi Fasan.   

Abstract

Engineered variants of the heme-containing protein myoglobin can efficiently catalyze the insertion of α-diazo esters into the N-H bond of arylamines, featuring a combination of high chemoselectivity, elevated turnover numbers, and broad substrate scope.

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Year:  2015        PMID： 25504318      PMCID： PMC4282819          DOI： 10.1039/c4cc08753d

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  19 in total

1.  Copper-catalyzed asymmetric N-H insertion reactions: couplings of diazo compounds with carbamates to generate alpha-amino acids.

Authors:  Elaine C Lee; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2007-09-18       Impact factor: 15.419

2.  The diazo route to diazonamide A. Studies on the indole bis-oxazole fragment.

Authors:  James R Davies; Peter D Kane; Christopher J Moody
Journal:  J Org Chem       Date:  2005-09-02       Impact factor: 4.354

3.  Cu(I)-carbenoid- and Ag(I)-Lewis acid-catalyzed asymmetric intermolecular insertion of alpha-diazo compounds into N-H bonds.

Authors:  Stephan Bachmann; Doris Fielenbach; Karl Anker Jorgensen
Journal:  Org Biomol Chem       Date:  2004-09-28       Impact factor: 3.876

4.  Improved cyclopropanation activity of histidine-ligated cytochrome P450 enables the enantioselective formal synthesis of levomilnacipran.

Authors:  Z Jane Wang; Hans Renata; Nicole E Peck; Christopher C Farwell; Pedro S Coelho; Frances H Arnold
Journal:  Angew Chem Int Ed Engl       Date:  2014-05-06       Impact factor: 15.336

5.  Ruthenium-catalyzed one-pot carbenoid N-H insertion reactions and diastereoselective synthesis of prolines.

Authors:  Qing-Hai Deng; Hai-Wei Xu; Angella Wing-Hoi Yuen; Zhen-Jiang Xu; Chi-Ming Che
Journal:  Org Lett       Date:  2008-03-20       Impact factor: 6.005

6.  Catalytic X-H insertion reactions based on carbenoids.

Authors:  Dennis Gillingham; Na Fei
Journal:  Chem Soc Rev       Date:  2013-06-21       Impact factor: 54.564

7.  Cytochrome P450-Catalyzed Insertion of Carbenoids into N-H Bonds.

Authors:  Z Jane Wang; Nicole E Peck; Hans Renata; Frances H Arnold
Journal:  Chem Sci       Date:  2014-02-01       Impact factor: 9.825

8.  Intramolecular C(sp(3))H amination of arylsulfonyl azides with engineered and artificial myoglobin-based catalysts.

Authors:  Melanie Bordeaux; Ritesh Singh; Rudi Fasan
Journal:  Bioorg Med Chem       Date:  2014-05-20       Impact factor: 3.641

9.  Haem accessibility in cytochrome P-450 from rabbit liver. A proton magnetic relaxation study by stereochemical probes.

Authors:  H Rein; A Maricic; G R Jänig; S Vuk-Pavlovic; B Benko; O Ristau; K Ruckpaul
Journal:  Biochim Biophys Acta       Date:  1976-09-28

10.  Highly enantioselective insertion of carbenoids into N-H bonds catalyzed by copper complexes of chiral spiro bisoxazolines.

Authors:  Bin Liu; Shou-Fei Zhu; Wei Zhang; Chao Chen; Qi-Lin Zhou
Journal:  J Am Chem Soc       Date:  2007-04-12       Impact factor: 15.419
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  40 in total

1.  Origin of high stereocontrol in olefin cyclopropanation catalyzed by an engineered carbene transferase.

Authors:  Antonio Tinoco; Yang Wei; John-Paul Bacik; Daniela M Carminati; Eric J Moore; Nozomi Ando; Yong Zhang; Rudi Fasan
Journal:  ACS Catal       Date:  2018-12-28       Impact factor: 13.084

Review 2.  Exploiting and engineering hemoproteins for abiological carbene and nitrene transfer reactions.

Authors:  Oliver F Brandenberg; Rudi Fasan; Frances H Arnold
Journal:  Curr Opin Biotechnol       Date:  2017-07-13       Impact factor: 9.740

3.  Mechanistic Investigation of Biocatalytic Heme Carbenoid Si-H Insertions.

Authors:  Rahul L Khade; Ajay L Chandgude; Rudi Fasan; Yong Zhang
Journal:  ChemCatChem       Date:  2019-05-08       Impact factor: 5.686

Review 4.  The Metal Drives the Chemistry: Dual Functions of Acireductone Dioxygenase.

Authors:  Aditi R Deshpande; Thomas C Pochapsky; Dagmar Ringe
Journal:  Chem Rev       Date:  2017-07-21       Impact factor: 60.622

5.  Nature's Machinery, Repurposed: Expanding the Repertoire of Iron-Dependent Oxygenases.

Authors:  Noah P Dunham; Frances H Arnold
Journal:  ACS Catal       Date:  2020-09-28       Impact factor: 13.084

Review 6.  Design of artificial metalloproteins/metalloenzymes by tuning noncovalent interactions.

Authors:  Shun Hirota; Ying-Wu Lin
Journal:  J Biol Inorg Chem       Date:  2017-12-07       Impact factor: 3.358

7.  Stereoselective olefin cyclopropanation under aerobic conditions with an artificial enzyme incorporating an iron-chlorin e6 cofactor.

Authors:  Gopeekrishnan Sreenilayam; Eric J Moore; Viktoria Steck; Rudi Fasan
Journal:  ACS Catal       Date:  2017-10-09       Impact factor: 13.084

8.  Identification of Mechanism-Based Inactivation in P450-Catalyzed Cyclopropanation Facilitates Engineering of Improved Enzymes.

Authors:  Hans Renata; Russell D Lewis; Michael J Sweredoski; Annie Moradian; Sonja Hess; Z Jane Wang; Frances H Arnold
Journal:  J Am Chem Soc       Date:  2016-09-14       Impact factor: 15.419

9.  Myoglobin-Catalyzed C-H Functionalization of Unprotected Indoles.

Authors:  David A Vargas; Antonio Tinoco; Vikas Tyagi; Rudi Fasan
Journal:  Angew Chem Int Ed Engl       Date:  2018-07-06       Impact factor: 15.336

10.  Chemoselective Cyclopropanation over Carbene Y-H Insertion Catalyzed by an Engineered Carbene Transferase.

Authors:  Eric J Moore; Viktoria Steck; Priyanka Bajaj; Rudi Fasan
Journal:  J Org Chem       Date:  2018-07-06       Impact factor: 4.354
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