PMID- 31793784
OWN - NLM
STAT- PubMed-not-MEDLINE
DCOM- 20201207
LR  - 20201214
IS  - 1520-6904 (Electronic)
IS  - 0022-3263 (Linking)
VI  - 85
IP  - 3
DP  - 2020 Feb 7
TI  - One Step Synthesis of Fmoc-Aminoacyl-N-alkylcysteine via the Ugi Four-Component 
      Condensation Reaction.
PG  - 1458-1465
LID - 10.1021/acs.joc.9b02433 [doi]
AB  - A prompt preparation method of the Fmoc-aminoacyl-N-alkylcysteine dipeptide by an 
      Ugi four-component condensation reaction is described. Through a reaction with a 
      commercially available Fmoc-amino acid, an amine, an isocyanide, and a 
      mercaptoacetaldehyde derivative, one step synthesis of dipeptides containing 20 
      kinds of natural amino acid residues was achieved, which avoided the problematic 
      N-alkylation of S-tritylcysteine and its coupling reaction. The dipeptide was 
      applied to the Fmoc-solid-phase peptide synthesis, and peptide thioesters were 
      successfully obtained in high efficiency via N-alkylcysteine (NAC)-assisted 
      thioesterification.
FAU - Asahina, Yuya
AU  - Asahina Y
AUID- ORCID: 0000-0001-6814-245X
AD  - Institute for Protein Research , Osaka University , Yamadaoka 3-2 , Suita 
      565-0871 , Japan.
FAU - Hojo, Hironobu
AU  - Hojo H
AUID- ORCID: 0000-0003-0916-1233
AD  - Institute for Protein Research , Osaka University , Yamadaoka 3-2 , Suita 
      565-0871 , Japan.
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
DEP - 20191216
PL  - United States
TA  - J Org Chem
JT  - The Journal of organic chemistry
JID - 2985193R
SB  - IM
EDAT- 2019/12/04 06:00
MHDA- 2019/12/04 06:01
CRDT- 2019/12/04 06:00
PHST- 2019/12/04 06:00 [pubmed]
PHST- 2019/12/04 06:01 [medline]
PHST- 2019/12/04 06:00 [entrez]
AID - 10.1021/acs.joc.9b02433 [doi]
PST - ppublish
SO  - J Org Chem. 2020 Feb 7;85(3):1458-1465. doi: 10.1021/acs.joc.9b02433. Epub 2019 
      Dec 16.