Cyclic dipeptides as building blocks for combinatorial libraries. Part 2: Synthesis of bifunctional diketopiperazines

Rodionov, I. L.; Rodionova, Ludmila N.; Байдакова, Л. К.; Romashko, Alla M; Balashova, T. A.; Иванов, В. Т.

doi:10.1016/s0040-4020(02)01021-9

Cited by 32 publications

(15 citation statements)

References 18 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The number of carbon atoms on the main circle of cyclic dipeptides depends on different amino acid residues [14]. Considering that the number of atoms on the main circle composed of most amino acid residues is six, the conformations of the sixmember circle of cyclic dipeptides is representative.…”

Section: Methods Of Calculation Target Objectsmentioning

confidence: 99%

Quantum chemical study of cyclic dipeptides

Zhu

Tang

Shi

et al. 2006

Int J of Quantum Chemistry

View full text Add to dashboard Cite

ABSTRACT:The preferred conformations of cyclic dipeptides were first studied systemically using the density functional theory (DFT) B3LYP method at the 6-31G(d) level. The structural characteristics of cyclic dipeptides were revealed, most of which have not been confirmed until now. Our studies showed that the six-member main circles of cyclic dipeptides composed of natural l-amino acid residues appeared as boat conformations. The important factors that influence conformations of cyclic dipeptides, such as molecular total energy, nuclear repulsion energy, molecular orbit, spatial effects, and reactive mechanism, are discussed in detail.

show abstract

Section: Methods Of Calculation Target Objectsmentioning

confidence: 99%

Quantum chemical study of cyclic dipeptides

Zhu

Tang

Shi

et al. 2006

Int J of Quantum Chemistry

View full text Add to dashboard Cite

show abstract

“…For combinatorial synthesis there has been a resurgence of interest in the Ugi reactions exemplified in Scheme 13 [76,77]. A new resinbound isonitrile has also been designed [78] for the Ugi 4CC reaction and has been shown to work according to Scheme 14. In the synthesis [79] of building blocks based on cyclo (Aax-Bbx) consisting of Glu or Asp (Aax) and Lys, Orn or Dab (Bbx), the authors have returned to conventional cyclization of linear dipeptide esters. However, cyclization was not so straightforward as anticipated, requiring long reaction times to reduce the amount of racemization detected when higher temperatures and shorter times had been used.…”

Section: Cyclodipeptides (Dioxo-or Diketo-piperazines)mentioning

confidence: 99%

The cyclization of peptides and depsipeptides

Davies

2003

Journal of Peptide Science

416

241

View full text Add to dashboard Cite

Constricting the peptide backbone into a more defined conformational form through cyclization is an activity evolved in nature and in synthetic work, the latter straddling only the most recent decades. The resulting conformational constraints increase the probability of an optimum response with bio-receptors. The purpose of this review is to highlight developments that have proved to be reasonably efficient in the macrocyclization of linear precursors into cyclic peptides and depsipeptides.

show abstract

“…as useful scaffolds for combinatorial chemistry) as well as various reaction chemistries and mechanisms for producing structural analogues and derivatives. [1,2] Moreover, their diverse occurrence, isolation and structure determination from natural sources (including micro-organisms, [3,4] higher mammals, [5,6] and in foods, [7] for example, beverages such as beer [8] ) have also attracted scientific interest. Unsurprisingly, their potential for pharmacological use has not escaped attention.…”

Section: Introductionmentioning

confidence: 99%

Vibrational spectra and crystal structure of the di‐amino acid peptide cyclo(L‐Met‐L‐Met): comparison of experimental data and DFT calculations

Mendham

Potter

Palmer

et al. 2009

J Raman Spectroscopy

View full text Add to dashboard Cite

Experimental Raman and FT-IR spectra of solid-state non-deuterated andN-deuterated samples of cyclo(L-Met-L-Met) are reported and discussed. The Raman and FT-IR results show characteristic amide I vibrations (Raman: 1649 cm −1 , infrared: 1675 cm −1 ) for molecules exhibiting a cis amide conformation. A Raman band, assigned to the cis amide II vibrational mode, is observed at ∼1493 cm −1 but no IR band is observed in this region. Cyclo(L-Met-L-Met) crystallises in the triclinic space group P1 with one molecule per unit cell. The overall shape of the diketopiperazine (DKP) ring displays a (slightly distorted) boat conformation. The crystal packing employs two strong hydrogen bonds, which traverse the entire crystal via translational repeats. B3-LYP/cc-pVDZ calculations of the structure of the molecule predict a boat conformation for the DKP ring, in agreement with the experimentally determined X-ray structure.

show abstract

Cyclic dipeptides as building blocks for combinatorial libraries. Part 2: Synthesis of bifunctional diketopiperazines

Cited by 32 publications

References 18 publications

Quantum chemical study of cyclic dipeptides

Quantum chemical study of cyclic dipeptides

The cyclization of peptides and depsipeptides

Vibrational spectra and crystal structure of the di‐amino acid peptide cyclo(L‐Met‐L‐Met): comparison of experimental data and DFT calculations

Contact Info

Product

Resources

About