PMID- 17020289
OWN - NLM
STAT- MEDLINE
DCOM- 20070627
LR  - 20181113
IS  - 1523-7060 (Print)
IS  - 1523-7052 (Electronic)
IS  - 1523-7052 (Linking)
VI  - 8
IP  - 21
DP  - 2006 Oct 12
TI  - Trisubstituted (E)-alkene dipeptide isosteres as beta-turn promoters in the 
      gramicidin S cyclodecapeptide scaffold.
PG  - 4731-4
AB  - [reaction: see text] A concise synthesis of a gramicidin S analogue with 
      trisubstituted (E)-alkene dipeptide isostere (TEADI) replacements at both 
      d-Phe-Pro positions was realized. Conformational analysis demonstrated that 
      TEADIs can serve as type II beta-turn promoters in a cyclic scaffold and 
      successfully mimic a proline residue.
FAU - Xiao, Jingbo
AU  - Xiao J
AD  - Department of Chemistry and Center for Chemical Methodologies & Library 
      Development, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.
FAU - Weisblum, Bernard
AU  - Weisblum B
FAU - Wipf, Peter
AU  - Wipf P
LA  - eng
GR  - P50 GM067082/GM/NIGMS NIH HHS/United States
GR  - P50 GM067082-01/GM/NIGMS NIH HHS/United States
PT  - Journal Article
PT  - Research Support, N.I.H., Extramural
PT  - Research Support, Non-U.S. Gov't
PL  - United States
TA  - Org Lett
JT  - Organic letters
JID - 100890393
RN  - 0 (Alkenes)
RN  - 0 (Dipeptides)
RN  - 0 (Peptides, Cyclic)
RN  - 1405-97-6 (Gramicidin)
RN  - 9DLQ4CIU6V (Proline)
SB  - IM
MH  - Alkenes/*chemistry
MH  - Dipeptides/*chemistry
MH  - Gramicidin/chemical synthesis/*chemistry
MH  - Molecular Mimicry
MH  - Molecular Structure
MH  - Peptides, Cyclic/chemical synthesis/*chemistry
MH  - Proline/chemistry
MH  - Protein Conformation
MH  - Protein Structure, Secondary
PMC - PMC2631548
MID - NIHMS61354
EDAT- 2006/10/06 09:00
MHDA- 2007/06/28 09:00
PMCR- 2009/01/27
CRDT- 2006/10/06 09:00
PHST- 2006/10/06 09:00 [pubmed]
PHST- 2007/06/28 09:00 [medline]
PHST- 2006/10/06 09:00 [entrez]
PHST- 2009/01/27 00:00 [pmc-release]
AID - 10.1021/ol0617704 [doi]
PST - ppublish
SO  - Org Lett. 2006 Oct 12;8(21):4731-4. doi: 10.1021/ol0617704.