PMID- 28111523
OWN - NLM
STAT- PubMed-not-MEDLINE
LR  - 20201001
IS  - 1434-193X (Print)
IS  - 1099-0690 (Linking)
VI  - 2016
IP  - 34
DP  - 2016 Dec
TI  - Native Serine Peptide Assembly: Scope and Utility.
PG  - 5633-5636
LID - 10.1002/ejoc.201601148 [doi]
AB  - This work develops serine peptide assembly (SPA), which complements and contrasts 
      with classic native chemical ligation (NCL). Advances in reagent-less peptide 
      bond formation have been applied to serine (and serine models) and a range of 
      C-terminal amino acids, including bulky residues that are not amenable to NCL. 
      The particular appeal of SPA is preparative-scale segment condensations with zero 
      racemization risk and favourable process mass intensity (PMI). Mechanistic 
      studies support a previously proposed reaction pathway via an initial 
      trans-esterification step. An understanding of the factors favouring this pathway 
      relies on hard-soft acid-base theory, where mildly activated esters with the 
      largest carbonyl positive charge are most reactive with hydroxy amines. Novel 
      C-terminal activators have been discovered that enhance reactivity and give 
      harmless by-products.
FAU - Pirrung, Michael C
AU  - Pirrung MC
AD  - Department of Chemistry, University of California, Riverside, CA 92521 USA.
FAU - Schreihans, Ryan S
AU  - Schreihans RS
AD  - Department of Chemistry, University of California, Riverside, CA 92521 USA.
LA  - eng
GR  - R21 AI106597/AI/NIAID NIH HHS/United States
PT  - Journal Article
DEP - 20161115
PL  - Germany
TA  - European J Org Chem
JT  - European journal of organic chemistry
JID - 9805750
PMC - PMC5241111
MID - NIHMS841196
OTO - NOTNLM
OT  - acylation
OT  - amides
OT  - amino acids
OT  - nucleophilic substitution
OT  - transesterification
EDAT- 2017/01/24 06:00
MHDA- 2017/01/24 06:01
PMCR- 2017/12/01
CRDT- 2017/01/24 06:00
PHST- 2017/01/24 06:00 [entrez]
PHST- 2017/01/24 06:00 [pubmed]
PHST- 2017/01/24 06:01 [medline]
PHST- 2017/12/01 00:00 [pmc-release]
AID - 10.1002/ejoc.201601148 [doi]
PST - ppublish
SO  - European J Org Chem. 2016 Dec;2016(34):5633-5636. doi: 10.1002/ejoc.201601148. 
      Epub 2016 Nov 15.