10
PÉREZ-MELLOR ET AL.
diketopiperazine. Nucleosides Nucleotides Nucleic Acids. 2004;
3(12):1815-1824.
0. Grande F, Garofalo A, Neamati N. Small molecules anti-HIV
therapeutics targeting CXCR4. Curr Pharm Des. 2008;14(4):
85-404.
46. Merten C, Kowalik T, Hartwig A. Vibrational circular dichro-
ism spectroscopy of solid polymer films: effects of sample ori-
entation. Appl Spectrosc. 2008;62(8):901-905.
47. Buffeteau T, Lagugne-Labarthet FS, Sourisseau C. Vibrational
circular dichroism in general anisotropic thin solid films: mea-
surement and theoretical approach. Appl Spectrosc. 2005;59(6):
732-745.
2
3
3
3
1. Walchshofer N, Sarciron ME, Garnier F, Delatour P,
Petavy AF, Paris J. Anthelmintic activity of 3,6-dibenzyl-
2
,5-dioxopiperazine, cyclo(L-Phe-L-Phe). Amino Acids. 1997;12
48. Cao XL, Fischer G. Infrared spectra of monomeric L-alanine
and L-alanine-N-d(3) zwitterions isolated in a KBr matrix.
Chem Phys. 2000;255(2–3):195-204.
(1):41-47.
3
2. Danda H. Essential factors in asymmetric hydrocyanation cata-
lyzed by cyclo (-(R)-Phe-(R)-His-). Synlett. 1991;1991(04):
49. Basiuk VA, Gromovoy TY, Glukhoy AM, Golovaty VG. Chemi-
cal-transformations of proteinogenic amino-acids during their
sublimation in the presence of silica. Orig Life Evol Biosph.
1991;21(3):129-144.
50. Kama AB, Genois R, Massuyeau F, Sidibe M, Diop CAK,
Gautier R. Cyclohexylammonium sulfanilate: a simple repre-
sentative of the chiral materials containing only achiral build-
ing units. Mater Lett. 2019;241:6-9.
51. Sunatsuki Y, Fujita K, Maruyama H, et al. Chiral crystal struc-
ture of a P2(1)2(1)2(1) kryptoracemate iron (II) complex with
an unsymmetric azine ligand and the observation of chiral sin-
gle crystal circular dichroism. Cryst Growth Des. 2014;14(8):
3692-3695.
2
63-264.
3
3. Tanaka K, Mori A, Inoue S. The cyclic dipeptide cyclo [(S)-
phenylalanyl-(S)-histidyl] as a catalyst for asymmetric addition
of hydrogen cyanide to aldehydes. J Org Chem. 1990;55(1):
1
81-185.
3
4. Gdaniec M, Liberek B. Structure of cyclo(-l-phenylalanyl-l-
phenylalanyl-). Acta Crystallograph Sec C-Crystal Struct
Commun. 1986;42:1343-1345.
5. Perez-Mellor A, Zehnacker A. Vibrational circular dichroism of
a 2,5-diketopiperazine (DKP) peptide: evidence for dimer for-
mation in cyclo LL or LD diphenylalanine in the solid state.
Chirality. 2017;29(2):89-96.
3
3
3
3
6. Garcia AM, Iglesias D, Parisi E, et al. And others. Chirality
effects on peptide self-assembly unraveled from molecules to
materials. Chem. 2018;4(8):1862-1876.
7. Ozawa Y, Sato H, Kayano Y, et al. Self-assembly of tripeptides
into c-turn nanostructures. Phys Chem Chem Phys. 2019;21(21):
52. Brizard A, Aime C, Labrot T, et al. Counterion, temperature,
and time modulation of nanometric chiral ribbons from
gemini-tartrate amphiphiles. J Am Chem Soc. 2007;129(12):
3754-3762.
53. Chang BS, Li X, Sun TL. Self-assembled chiral materials from
achiral components or racemates. Eur Polym J. 2019;118:
365-381.
54. Gautier R, Klingsporn JM, Van Duyne RP, Poeppelmeier KR.
Optical activity from racemates. Nat Mater. 2016;15(6):591-592.
55. Quesada-Moreno MM, Cruz-Cabeza AJ, Aviles-Moreno JR,
et al. The curious case of 2-propy1-1H-benzimidazole in the
solid state: an experimental and theoretical study. J Phys Chem
A. 2017;121(30):5665-5674.
56. Asselin P, Madebene B, Soulard P, et al. Competition between
inter- and intra-molecular hydrogen bonding: an infrared spec-
troscopic study of jet-cooled amino-ethanol and its dimer.
J Chem Phys. 2016;145(22).
1
0879-10883.
8. Abo-Riziq AG, Bushnell JE, Crews B, Callahan MP, Grace L,
de Vries MS. Discrimination between diastereoisomeric dipep-
tides by IR-UV double resonance spectroscopy and ab initio
calculations. Int J Quantum Chem. 2005;105(4):437-445.
9. Pérez Mellor A, Zehnacker A. Chirality effects in jet-cooled
cyclic dipeptides. In: Ebata T, Fujii M, eds. Physical Chemistry
of Cold Gas-Phase Functional Molecules and Clusters. Singa-
pore: Springer; 2019:63-87.
3
4
0. Alata I, Perez-Mellor A, Ben Nasr F, et al. Does the residues
chirality modify the conformation of a cyclo-dipeptide? Vibra-
tional spectroscopy of protonated cyclo-diphenylalanine in the
gas phase. J Phys Chem A. 2017;121(38):7130-7138.
57. Oswald S, Seifert NA, Bohle F, et al. The chiral trimer and a
metastable chiral dimer of achiral hexafluoroisopropanol: a
multi-messenger study. Angewandte Chemie Int Ed. 2019;58
(15):5080-5084.
4
1. Dunbar RC, Steill JD, Oomens J. Chirality-induced conforma-
tional preferences in peptide-metal ion binding revealed by IR
spectroscopy. J Am Chem Soc. 2011;133(5):1212-1215.
4
2. Lepere V, Le Barbu-Debus K, Clavaguera C, et al. Chirality-
dependent structuration of protonated or sodiated
polyphenylalanines: IRMPD and ion mobility studies. Phys
Chem Chem Phys. 2016;18(3):1807-1817.
58. Bodansky M. Principles of Peptides Synthesis. Berlin: Springer
Verlag; 1984.
59. Zhu YY, Tang MS, Shi XY, Zhao YF. Quantum chemical study
of cyclic dipeptides. Int J Quantum Chem. 2007;107(3):745-753.
60. Xia P, Wang C, Qi C. Theoretical study on the cyclization
mechanism of dipeptides. Chin J Chem. 2013;31(6):813-818.
61. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA,
Cheeseman JR, Scalmani G, Barone V, Mennucci B,
Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP,
Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M,
Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M,
Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T,
Montgomery JA, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ,
Brothers E, Kudin KN, Staroverov VN, Kobayashi R,
Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS,
4
3. Moss J, Bundgaard H. Kinetics and mechanism of the facile
cyclization of histidyl-prolineamide to cyclo (his-pro) in
aqueous-solution and the competitive influence of human
plasma. J Pharm Pharmacol. 1990;42(1):7-12.
4
4. Capasso S, Vergara A, Mazzarella L. Mechanism of
2
,5-dioxopiperazine formation. J Am Chem Soc. 1998;120(9):
1
990-1995.
4
5. Szardenings AK, Burkoth TS, Lu HH, Tien DW, Campbell DA.
simple procedure for the solid phase synthesis of
A
diketopiperazine and diketomorpholine derivatives. Tetrahe-
dron. 1997;53(19):6573-6593.