[System] polypeptide self-assembly literature information extraction

[User]
Boc-Ser-Val-Gly-OCH(2)Ph (31) showed high gelation abilities in the aromatic
solvents, particularly in toluene. The minimum gelation concentration of 31 in
toluene was 10 mg/ml, suggesting that 2500 molecules of toluene were immobilized
by each molecule of the tripeptide 31. The FT-IR data indicated that formation
of antiparallel beta-sheets through intermolecular hydrogen bonding was central
to the generation of nanofibers during gelation.

Boc-Ser-Val-Gly-OCH2Ph  (31)  showed  high  gelation  abilities  in  the  aromatic  solvents,  particularly  in
toluene. The minimum gelation concentration of 31 in toluene was 10 mg/ml, suggesting that 2500 molecules of
toluene were immobilized by each molecule of the tripeptide 31. The FT-IR data indicated that formation of an-
tiparallel bb-sheets through intermolecular hydrogen bonding was central to the generation of nanoﬁbers during
gelation.
Low  molecular  weight  (supramolecular)  gels  have  at-
tracted  attention  in  the  ﬁelds  of  supramolecular  chemistry
and  material  chemistry  over  the  past  two  decades.1—6) The
gel phase is a wettable viscoelastic physical state that shares
some properties of both liquid and solid phases. Gelation oc-
curs  when  self-organizing  gelators  produce  an  entangled
three-dimensional  network  of  ﬁbers  that  constrains  the  mo-
bility  of  the  embedded  solvent  molecules.  Low  molecular
weight  gelators  based  on  amino  acids,7—10) ureas,11—13)
amides,14—16) and saccharides17—19) have been developed, and
the  responses  of  these  gels  to  photo  irradiation,20,21) ultra-
sonic  frequencies,22,23) and  biologically  active  agents10,24,25)
have  been  described.  However,  organic  reactions  (covalent
bond forming reactions) in the gel phase have received rela-
tively little attention.26,27) We are trying to develop novel or-
ganic  reactions  in  a  supramolecular  gel  phase  using  a  dual-
functional molecule that is capable of catalyzing reaction as
well as forming gel. In this paper, we describe the synthesis
and  gelation  properties  of  several  tripeptide  derivatives,
which form the backbone of the dual-functional molecule.
N-t-Butoxycarbonyl  (Boc)  and  O-benzyl  protected  tripep-
tide gelators, composed of Gly, Ala, and Val, were designed
because  this  combination  was  previously  and  accidentally
shown  to  yield  interesting  gelation  properties.28) Twenty-
seven  tripeptides,  1—27,  based  on  various  combinations  of
Gly,  Ala,  and  Val,  were  synthesized  by  repeated  condensa-
tion  and  deprotection  in  the  liquid  phase  (Chart  1).29—31)
Each  amino  acid  benzyl  ester  (third  fragment)  was  reacted
with  a  Boc-protected  amino  acid  (second  fragment)  under
1-hydroxybenzotriazole  hydrate  (HOBt · H2O)/1-ethyl-3-(3-
dimethylaminopropyl)  carbodiimide  hydrochloride  (EDAC ·
HCl)/triethylamine  conditions  in  27%  to  quantitative  yields.
The  dipeptide  was  subsequently  deprotected  by  removal  of
the Boc group in HCl/dioxane to give an O-benzyl dipeptide.
A Boc-protected amino acid (ﬁrst fragment) was then intro-
duced to the dipeptide under similar conditions to afford the
desired tripeptides 1—27 in yields of 15—99%.
The  gelation  abilities  of  the  27  tripeptide  derivatives  in
each  of  ten  organic  solvents  (hexane,  EtOAc,  CHCl3,
CH2Cl2,  acetone,  acetonitrile,  EtOH,  MeOH,  toluene,  and
chlorobenzene)  were  surveyed  as  follows.  Each  tripeptide/
solvent  combination  was  mixed  in  a  microtube  and  (as  ap-
propriate)  irradiated  with  ultrasound  for  30 min  at  tempera-
tures ranging from room temperature to 60 °C to afford a ho-
mogeneous solution. The solutions were stored in an incuba-
tor at 20 °C for 24 h. When the tube was inverted and tapped,
the absence of a ﬂuid phase was deﬁned as a gel (transparent
or opaque gel), and a crumpled jelly object was deﬁned as a
partial  gel.  Table  1  shows  the  results  of  the  ﬁrst  screening
and  the  minimum  gelation  concentration  for  those  tripep-
tide/solvent combinations that yielded a gel.
The  results  shown  in  Table  1  indicate  that  toluene  and
chlorobenzene, which have aromatic rings, showed the high-
est propensity for gelation among the solvents assayed, sug-
gesting that a p–p interaction between the aromatic rings of
the  solvent  and  the  benzyl  group  of  the  tripeptide  played  a
crucial role in gelation. The tripeptide sequences X-Val-Gly
7—9 and X-Ala-Ala 13—15 displayed inherently high gela-
tion abilities for these solvents.
A new series of tripeptides with the sequences X-Val-Gly
and X-Ala-Ala were synthesized and examined in detail. For
the N-terminal amino acid (X), serine and glutamine were se-
lected  because  of  their  hydrogen  bonding  abilities,  and
phenylalanine  was  selected  for  its  ability  to  engage  in p–p
stacking  interactions.  Tripeptides  28—33 were  synthesized
via the route described in Chart 1. The results from a second
gelation screening assay, using the additional solvents o-, m-,
and p-xylenes as aromatic solvents in addition to the solvents
assayed in the ﬁrst screening, are summarized in Table 2.
Among  these  tripeptides,  Boc-Ser-Val-Gly-OCH2Ph  (31)
showed excellent gelation properties in the aromatic solvents,
particularly  in  toluene  (Fig.  1a),  most  likely  because  of  the
The concentration of the tripeptide was up to 100 mg/ml. The minimum gelation concentration (mg/ml) is shown in a parenthesis. h: homogeneous solution; T: transparent gel;
The concentration of the tripeptide was up to 100 mg/ml. The minimum gelation concentration (mg/ml) is shown in a parenthesis. h: homogeneous solution; T: transparent gel;
additional  hydrogen  bonding  capacity  introduced  by  the  hy-
droxy group of serine. The minimum gelation concentration
of  31 in  toluene  was  10 mg/ml,  suggesting  that  2500  mole-
cules  of  toluene  were  immobilized  by  each  molecule  of  the
tripeptide 31.
Boc-Ser-Val-Gly-OCH2Ph  (31)  yielded  the  best  gelation
properties,  and  the  morphological  characteristics  of  its
toluene  gel  were  observed  by  scanning  electron  microscopy
(SEM),  three-dimensional  (3D)  laser  scanning  optical  mi-
croscopy  and  digital  optical  microscopy  (Fig.  1).  SEM  re-
vealed a plate-like microcrystalline structure (1 mm in width,
Fig.  1b).  3D  laser  microscopy  revealed  a  network  of  entan-
gled nanoﬁbers, the minimum height of which was estimated
to be 60—70 nm (Fig. 1c). The imaging conditions were re-
sponsible  for  the  observation  of  two  morphologies,  micro-
crystals  or  nanoﬁbers,  for  the  toluene  gel  of  31.  3D  optical
imaging permitted observation of the ﬁbers under wet condi-
tions (in the presence of solvent). The SEM measurement re-
quired  solvent  removal  under  reduced  pressure,  which  in-
duced  the  nanoﬁbers  to  form  a  microcrystalline  phase.  3D
optical  imaging  was  used  to  follow  the  nanoﬁber-to-micro-
crystal  transition  (Fig.  1d).  A  digital  optical  microscope,  in
which  the  gel  remained  wet,  also  revealed  long  ﬁbers  (Fig.
The intermolecular interactions involved in stabilizing the
toluene gel of 31 were characterized by  1H-NMR. The short
transversal  relaxation  time  in  the  gel  state  prevented  collec-
tion of the gel state NMR spectrum of gelator 31. We there-
fore  inferred  the  intermolecular  interactions  and  driving
force  for  gelation  of  31 by  measuring  the  solution-phase
NMR spectrum as a function of temperature and concentra-
tion of 31 (Fig. 2). At 40 °C, 5 mg/ml 31 in toluene d-8, three
signals  corresponding  to  the  NH  protons  (Ha,  Hb,  Hc  indi-
cated in the structure of Fig. 2) were observed at d 7.18 (Hb),
6.69 (Hc), and 5.67 (Ha), respectively (all shifts are given in
ppm).  As  the  concentration  of  31 increased  and/or  the  tem-
(a) A photograph of a toluene gel of 31 (10 mg/ml). (b) SEM image of microcrystals
of 31, formed during sample drying. (c, d) 3D scanning laser images of the toluene gel
(wet state). (e) Digital microscopy of the toluene gel (wet state).
The time course IR spectra of 31 at 3200—3450 cm(cid:2)1 (in
the region of amide A) is shown in Fig. 3a. As the solution
phase  transitioned  to  the  gel  phase,  the  strength  of  the  free
NH  stretch  at  3410 cm(cid:2)1 decreased  and  the  strength  of  the
hydrogen  bonding  NH  stretch  (3319 cm(cid:2)1)  increased  with
an  isosbestic  point.  At  1500—1800 cm(cid:2)1 (amide  I  and  II
regions, Fig. 3b), the strength of the free carbonyl stretch at
1678 cm(cid:2)1 decreased  with  a  concomitant  increase  in  the
strength  of  the  hydrogen  bonding  carbonyl  stretch  at  1645
cm(cid:2)1, with several isosbestic points. Yamada and coworkers
reported that parallel or antiparallel b-sheet secondary struc-
tures of (tri-)peptides could be distinguished by the presence
or absence, respectively, of the characteristic IR absorption at
1690 cm(cid:2)1 in  addition  to  the  absorptions  at  1630 cm(cid:2)1 and
1527 cm(cid:2)1,  independent  of  the  sequence.32,33) Taking  into
consideration  of  their  data,  in  the  solution  phase,  tripeptide
31 absorbed  at  3410,  1678,  and  1495 cm(cid:2)1,  indicating  the
absence  of  speciﬁc  secondary  structure.  In  contrast,  the  gel
phase  showed  absorptions  at  3318,  1681,  1645,  and  1527
cm(cid:2)1, suggesting the formation of antiparallel b sheets.
In  conclusion,  we  synthesized  27  tripeptides  (combina-
tions of Gly, Ala, and Val) for a ﬁrst screening assay, and 6
tripeptides for a second screening assay, to test for gelation in
organic  solvents.  We  identiﬁed  Boc-Ser-Val-Gly-OCH2Ph
(31)  as  an  excellent  gelator  for  aromatic  solvents.  Boc-Ser-
Val-Gly-OCH2Ph (31) yielded particularly high gelation abil-
ities  in  toluene,  with  a  minimum  gelation  concentration  of
10 mg/ml.  The  FT-IR  data  suggested  that  formation  of  an-
tiparallel b-sheets through intermolecular hydrogen bonding
was  central  to  the  generation  of  nanoﬁbers  during  gelation.
Identiﬁcation  and  characterization  of  the  gelation  properties
of  31 lay  the  foundation  for  developing  a  dual-functional
molecule  that  displays  both  catalytic  activity  and  gelation
Tripeptides  1—33 were  synthesized  by  the  procedure  described  in  the
text.29—31) FT-IR  spectra  of  31 were  collected  on  a  JASCO  FT/IR-4200,
using  a  NaCl  liquid  cell  (0.1 mm  path  length)  with  toluene  d-8.  SEM,  3D
scanning  laser  microscopy,  and  digital  optical  microscopy  were  performed
using a VE-9800 SEM, a VK-9700 Generation II Color Laser Scanning Mi-
croscope, and a VHX-1000 (KEYENCE) digital optical microscope, respec-

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