PMID- 19810693
OWN - NLM
STAT- MEDLINE
DCOM- 20100112
LR  - 20240312
IS  - 1520-6904 (Electronic)
IS  - 0022-3263 (Print)
IS  - 0022-3263 (Linking)
VI  - 74
IP  - 21
DP  - 2009 Nov 6
TI  - Synthesis of a cyclic pentapeptide mimic of the active site His-Tyr cofactor of 
      cytochrome c oxidase.
PG  - 8212-8
LID - 10.1021/jo901744y [doi]
AB  - Arylboronic acid based technology provides a mild, regioselective, and nontoxic 
      N-arylation procedure for accessing the unusual N-arylated side chain histidine 
      found in the active site of cytochrome c oxidase (CcO). The N-arylated histidine 
      is elaborated to the complete cytochrome c oxidase cyclic pentapeptide cofactor. 
      Molecular modeling of the cofactor provides insight into the dynamic character of 
      the N-aryl bond.
FAU - Mahoney, Maximillian E
AU  - Mahoney ME
AD  - Department of Chemistry and Biochemistry, University of California, Santa Cruz, 
      California 95064, USA.
FAU - Oliver, Allen
AU  - Oliver A
FAU - Einarsdottir, Olof
AU  - Einarsdottir O
FAU - Konopelski, Joseph P
AU  - Konopelski JP
LA  - eng
GR  - S10 RR019918/RR/NCRR NIH HHS/United States
GR  - GM53788/GM/NIGMS NIH HHS/United States
GR  - S10RR019918/RR/NCRR NIH HHS/United States
GR  - R01 GM053788-12/GM/NIGMS NIH HHS/United States
GR  - R01 GM053788/GM/NIGMS NIH HHS/United States
PT  - Journal Article
PT  - Research Support, N.I.H., Extramural
PT  - Research Support, U.S. Gov't, Non-P.H.S.
PL  - United States
TA  - J Org Chem
JT  - The Journal of organic chemistry
JID - 2985193R
RN  - 0 (Oligopeptides)
RN  - 4QD397987E (Histidine)
RN  - EC 1.9.3.1 (Electron Transport Complex IV)
RN  - K3Z4F929H6 (Lysine)
SB  - IM
MH  - Catalytic Domain
MH  - Crystallography, X-Ray
MH  - Electron Transport Complex IV/chemistry/*metabolism
MH  - Histidine/*chemistry
MH  - Lysine/*chemistry
MH  - Magnetic Resonance Spectroscopy
MH  - Mass Spectrometry
MH  - Models, Molecular
MH  - *Molecular Mimicry
MH  - Oligopeptides/*chemical synthesis/chemistry
MH  - Protein Conformation
MH  - Spectrophotometry, Infrared
PMC - PMC2783554
MID - NIHMS151476
EDAT- 2009/10/09 06:00
MHDA- 2010/01/13 06:00
PMCR- 2010/11/06
CRDT- 2009/10/09 06:00
PHST- 2009/10/09 06:00 [entrez]
PHST- 2009/10/09 06:00 [pubmed]
PHST- 2010/01/13 06:00 [medline]
PHST- 2010/11/06 00:00 [pmc-release]
AID - 10.1021/jo901744y [doi]
PST - ppublish
SO  - J Org Chem. 2009 Nov 6;74(21):8212-8. doi: 10.1021/jo901744y.