PMID- 22059552
OWN - NLM
STAT- MEDLINE
DCOM- 20120501
LR  - 20131121
IS  - 1520-6904 (Electronic)
IS  - 0022-3263 (Linking)
VI  - 76
IP  - 24
DP  - 2011 Dec 16
TI  - Stereoselective synthesis of uridine-derived nucleosyl amino acids.
PG  - 10083-98
LID - 10.1021/jo201935w [doi]
AB  - Novel hybrid structures of 5'-deoxyuridine and glycine were conceived and 
      synthesized. Such nucleosyl amino acids (NAAs) represent simplified analogues of 
      the core structure of muraymycin nucleoside antibiotics, making them useful 
      synthetic building blocks for structure-activity relationship (SAR) studies. The 
      key step of the developed synthetic route was the efficient and highly 
      diastereoselective asymmetric hydrogenation of didehydro amino acid precursors 
      toward protected NAAs. It was anticipated that the synthesis of unprotected 
      muraymycin derivatives via this route would require a suitable intermediate 
      protecting group at the N-3 of the uracil base. After initial attempts using PMB- 
      and BOM-N-3 protection, both of which resulted in problematic deprotection steps, 
      an N-3 protecting group-free route was envisaged. In spite of the pronounced 
      acidity of the uracil-3-NH, this route worked equally efficient and with 
      identical stereoselectivities as the initial strategies involving N-3 protection. 
      The obtained NAA building blocks were employed for the synthesis of truncated 
      5'-deoxymuraymycin analogues.
FAU - Spork, Anatol P
AU  - Spork AP
AD  - Department of Chemistry, Institute of Organic and Biomolecular Chemistry, 
      Georg-August-University Gottingen, Tammannstr. 2, 37 077 Gottingen, Germany.
FAU - Wiegmann, Daniel
AU  - Wiegmann D
FAU - Granitzka, Markus
AU  - Granitzka M
FAU - Stalke, Dietmar
AU  - Stalke D
FAU - Ducho, Christian
AU  - Ducho C
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
DEP - 20111121
PL  - United States
TA  - J Org Chem
JT  - The Journal of organic chemistry
JID - 2985193R
RN  - 0 (Amino Acids)
RN  - 0 (Anti-Bacterial Agents)
RN  - 0 (Nucleotides)
RN  - 0 (Peptides)
RN  - 0 (muraymycin A1)
RN  - 8W8T17847W (Urea)
RN  - W78I7AY22C (Deoxyuridine)
SB  - IM
MH  - Amino Acids/*chemistry
MH  - Anti-Bacterial Agents/analysis/*chemical synthesis/pharmacology
MH  - Deoxyuridine/*chemistry
MH  - Humans
MH  - Hydrogenation
MH  - Magnetic Resonance Spectroscopy
MH  - Molecular Structure
MH  - Nucleotides/chemistry
MH  - Peptides/chemistry
MH  - Stereoisomerism
MH  - Structure-Activity Relationship
MH  - Urea/chemistry
EDAT- 2011/11/09 06:00
MHDA- 2012/05/02 06:00
CRDT- 2011/11/09 06:00
PHST- 2011/11/09 06:00 [entrez]
PHST- 2011/11/09 06:00 [pubmed]
PHST- 2012/05/02 06:00 [medline]
AID - 10.1021/jo201935w [doi]
PST - ppublish
SO  - J Org Chem. 2011 Dec 16;76(24):10083-98. doi: 10.1021/jo201935w. Epub 2011 Nov 
      21.