多肽合成中困难序列的缩合研究进展(3)
时间:2025-03-10
时间:2025-03-10
非常详细的综述性文章
HANXiang,etal:Recent
progressintheimprovementofthecouplingefficiency
peptidesynthesis
of“difficultsequences’’in
’113
sequences”is
reversibleamide—backbonesubstitution.involvesN—substitution
of
one
leeular
reactive
acyltransfer
mechanism.Moreover
themore
Thisstrategy
ormore
or
Hnb(2一hydroxy-4一nitrobenzyl)
auxiliaries
have
been
uses
a
backbone
amidebondsofseveralresiduesbeforetheidentifiedexpected“difficult
sequences”in
a
protecting
introduced(Figure
nitrosame
peptide
is
to
31[13-.TheHnb
assist
auxillaryand
substituenttoadvantageous
sequences”.
encountered.Amide—backbonesubstitutionappears
prevent
or
acyltransfer
as
hasthe
disrupttroublesomeintermolecularhydrogen—
native
effectHmbfor
to
overcoming“difficult
bondingnetworksbythe
removaloftheamide
Compared
the
Hmbauxiliary,obviously
improved
hydrogenbondafterN—substitution,whichalterationofthebackboneconformationistionoftertiaryamidebonds.
The
solubility
improvement
is
attributed
to
acyltransferreactivity,especiallybranched
amino
acids,with
the
betweenlargeor卢一Hnbauxiliary
of
was
causedbytheintroduc—
obtained(Figure4).After
the
sequence,the
temporary
synthesisexpected
can
protectinggroupHnb
at
be
existenceoftertiaryamidebonds,X一(Z)Y,whereXandY
are
convenientlyremovedbymildphotolysisThe
oxidative—reductive
safety
catch
366nm[141.SiMb
arbitraryamino
acidresiduesandZis
a
(3一
temporary
causes
protectinggroup.The
of
tertiaryamide
structure
bondthethiscalled
methylsulfinyl-4一methoxy一6一hydroxybenzyl)backbone
auxiliaryalso
can
disturbanceof
tertiary
the卢一sheet
amide
bond
by
usedforthispurpose(Figure3)’15|.
rotation
plane
and
TheAib(o/。aminoisobutvricacid)residueusedin
peptidesynthesisisanothereffect.TheabilityofAibthe
solvation
of
to
case
segmentation“peptide
from卢一sheet
segment
structureswasthat
can
offerthePSS
separation
(PSS)”.Drab
is
promote