- Solar and Visible Light Assisted Peptide Coupling
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Amino acid and peptide couplings are widely used in fields related to pharma and materials. Still, current peptide synthesis continues to rely on the use of expensive, water sensitive, and waste-generating coupling reagents, which are often prepared in mu
- Mishra, Abhaya K.,Parvari, Galit,Santra, Sourav K.,Bazylevich, Andrii,Dorfman, Ortal,Rahamim, Jonatan,Eichen, Yoav,Szpilman, Alex M.
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supporting information
p. 12406 - 12412
(2021/04/05)
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- Influence of the dipeptide linker configuration on the activity of PSMA ligands
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Selective ligands of an urea-based prostate specific membrane antigen with a phenylalanine/tyrosine-based dipeptide linker and with a mingled chiral centers configuration and/or substituted aromatic fragments were prepared in seven steps by liquid- and in
- Uspenskaya, Anastasiya A.,Machulkin, Alexey E.,Nimenko, Ekaterina A.,Shafikov, Radik R.,Petrov, Stanislav A.,Skvortsov, Dmitry A.,Beloglazkina, Elena K.,Majouga, Alexander G.
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p. 756 - 759
(2021/01/12)
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- Synthesis and Characterization of a Series of Orthogonally Protected l-Carnosine Derivatives
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l-Carnosine (β-alanyl-l-histidine) is an endogenous dipeptide that has been recognized for its broad spectrum of beneficial biological activities. However, the therapeutic utility of molecule has been hampered by its instability in human plasma (half-life
- El-Dakdouki, Mohammad H.,Daouk, Nadine,Abdallah, Hiba
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- Diphenylsilane as a coupling reagent for amide bond formation
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A simple procedure for amide bond formation using diphenylsilane as a coupling reagent is described. This methodology enables the direct coupling of carboxylic acids with primary and secondary amines, releasing only hydrogen and a siloxane as by-products. Only one equivalent of each partner is needed, providing a more sustainable amidation method producing minimal wastes. This methodology was also extended to the synthesis of peptides and lactams by addition of Hünig's base (DIPEA) and 4-dimethylaminopyridine (DMAP).
- Sayes, Morgane,Charette, André B.
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supporting information
p. 5060 - 5064
(2017/11/09)
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- High penetration prodrug compositions of peptides and peptide-related compounds
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The invention provides compositions of novel high penetration compositions (HPC) or high penetration prodrugs (HPP) of peptides and peptide-related compounds, which are capable of crossing biological barriers with higher penetration efficiency comparing t
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Page/Page column 78
(2016/02/26)
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- PEG prodrug of gambogic acid: Amino acid and dipeptide spacer effects
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The clinical application of gambogic acid (GA), a natural component with promising antitumor activity, was limited due to its extremely poor aqueous solubility, rapid elimination in vivo, and wide biodistribution. To solve these problems, 30 poly(ethylene
- Ding, Ya,Zhang, Peng,Tang, Xiao-Yan,Zhang, Can,Ding, Song,Ye, Hai,Ding, Qi-Long,Shen, Wen-Bin,Ping, Qi-Neng
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experimental part
p. 1694 - 1702
(2012/08/08)
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- Guanidine hydrochloride as an organocatalyst for N-Boc protection of amino groups
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A simple and efficient method for the chemoselective N-Boc protection of the amine moiety in a variety of compounds is described using di-tert-butyl dicarbonate and guanidine hydrochloride as an organocatalyst in ethanol at 35-40°C. Selective mono-N-Boc protection of diamines and chemoselective protection of hydroxylamines without formation of any side products is achieved. Amino acids and peptides are N-Boc protected efficiently in excellent yields under convenient reaction conditions.
- Jahani, Fatemeh,Tajbakhsh, Mahmood,Golchoubian, Hamid,Khaksar, Samad
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supporting information; experimental part
p. 1260 - 1264
(2011/04/15)
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- A convenient route to diversely substituted icosahedral closomer nanoscaffolds
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The design and synthesis of icosahedral polyhedral borane closomer motifs based upon carbonate and carbamate anchoring groups for biomedical applications are described. Dodecacarbamate closomers containing easily accessible groups of interest at their linker termini were synthesized via activation of the B-OH vertices as aryl carbonates and their subsequent reaction with primary amines. Novel dodecacarbonate closomers were successfully synthesized for the first time by reacting [closo-B12(OH)12]2- with an excess of respective aryl chloroformates, utilizing relatively short reaction times, mild conditions and simple purification strategies, all of which had previously presented difficulties in closomer chemistry. This methodology for the 12-fold degenerate synthesis of carbonate and carbamate closomers will greatly facilitate further exploration of closomers as monodisperse nanomolecular delivery platforms.
- Jalisatgi, Satish S.,Kulkarni, Vikas S.,Tang, Betty,Houston, Zachary H.,Lee, Mark W.,Hawthorne, M. Frederick
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supporting information; scheme or table
p. 12382 - 12385
(2011/10/02)
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- Microwave-assisted chemical ligation of S-acyl peptides containing non-terminal cysteine residues
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An efficient approach for the synthesis of a series of S-acyl peptides containing internal cysteine residues has been developed and the chemical long-range ligation of these S-acyl peptides via 5-, 8-, 11- and 14-membered cyclic transition states has been
- Hansen, Finn K.,Ha, Khanh,Todadze, Ekaterina,Lillicotch, Aaron,Frey, Alexander,Katritzky, Alan R.
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supporting information; experimental part
p. 7162 - 7167
(2011/11/14)
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- Water-soluble tripeptide Aβ (9-11) forms amyloid-like fibrils and exhibits neurotoxicity
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(Chemical Equation Presented) A water-soluble, hydrophilic tripeptide GYE, having sequence identity with the N-terminal segment of amyloid peptides Aβ(9-11), upon self-association exhibits amyloid-like fibrils and significant neurotoxicity towards the Neu
- Naskar, Jishu,Drew, Michael G. B.,Deb, Ishani,Das, Sumantra,Banerjee, Arindam
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supporting information; experimental part
p. 2625 - 2628
(2009/05/30)
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- TRANSDERMAL DELIVERY SYSTEMS OF PEPTIDES AND RELATED COMPOUNDS
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The novel positively charged pro-drugs of peptides and related compounds in the general formula (1) 'Structure 1' were designed and synthesized. The compounds of the general formula (1) 'Structure 1' indicated above can be prepared by standard peptide syn
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Page/Page column 16-17
(2008/12/05)
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- Synthesis and biological activity of branched enkephalin analogues
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The synthesis and biological activity of a new type of enkephalin analogs are reported. A series of branched pentapeptides of the enkephalin sequence with replacement of 2-glycine by D-ornithine and branching of the peptide chain in position 2 by attachment of proline, leucine, asparagine or methionine residues to the 8-amino group of D-ornithine were synthesized by classical solution methodology. Analgesic activity of the new analogs was assayed by the 'tail pinch' method following intracisternal and intravenous administrations to mice. They showed higher analgesic potency and longer duration of action as compared to linear and cyclic pentapeptides with the same amino acid composition. The activity determined in the GPI and MVD bioassays, and in a binding assay, revealed the preference of the branched analogs for the μ-type of opioid receptor over the δ-type. These results raise the possibility to synthesize enkephalin analogs with high analgesic potency and opiate receptor selectivity by varying the chemical character and length of the side chain in the 2-position.
- Bobrova, Irina,Abissova, Natalia,Mishlakova, Natalia,Rozentals, Guntis,Chipens, Gunar
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p. 255 - 266
(2007/10/03)
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- Synthesis of novel morphinan peptides based on ethenoisomorphinans and enkephalin residues containing L- and D-phenylalanine; conformational analysis and preliminary pharmacology (Chemistry of opium alkaloids, Part XXXIII)
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The morphinan peptides N-(4,5α-epoxy-3,6-dihydroxy-17-methyl-6α,14α-ethenoisomorphinan-7α-carbonyl)-L-phenylalanine ethyl ester (4), N-(4,5α-epoxy-3,6-dihydroxy-17-methyl-3,6-dihydroxy-17-methyl-6α,14α-ethenoisomorphinan-7α-carbonyl)glycinyl>-L-phenylalanine ethyl ester (6) have been prepared from 4,5α-epoxy-3,5-dimethoxy-17-methyl-6α,14α-ethenoisomorphinan-7α-carboxylic acid (7) and the protected amino acids.The morphinan moiety was coupled to the peptide residue via the acid chloride of 7, after which the morphinan peptides were O-demethylated with the aid of hydrogen bromide in glacial acetic acid.The dipeptide N-glycinyl-L-phenylalanine ethyl ester was synthesized via the Excess Mixed Anhydride method (EMA).The new morphinan peptides have been characterized by 1H and 13C NMR spectroscopy.For conformational analysis, the relative stabilities of two possible hydrogen bonds around the C7-C20 bond have been calculated on a model compound 11, using molecular mechanics.
- Cappon, J. J.,Lie, T. S.,Maat, L.
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p. 413 - 418
(2007/10/02)
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- USE OF 4-CHLOROBUTYL ESTERS IN PEPTIDE SYNTHESIS
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Ho and Wong synthesised 4-chlorobutyl esters of simple carboxylic acids and removed the ester group by the action of sodium sulfide under reflux conditions.We describe here the synthesis of the 4-chlorobutyl esters of glycine and L-phenylalanine and its use in the synthesis of six new N-protected dipeptides 4-chlorobutyl esters (XHNCH2CO-HNCHRCO2(CH2)4Cl; R = H, CH2Ph; X = Z, Boc, Trt).The selective removal of the 4-chlorobutyl group can be achieved by the action of the sulfide anion in aqueous acetonitrile (room temperature, 1.5 to 5 h).The conditions are milder than those described, but similar to the conditions used with the dipeptides 2-bromoethyl esters.The N-protected dipeptides were isolated in 50 to 80percent yield.
- Trigo, M. Joaquina S. A. Amaral,Santos, M. Isabel A. Oliveira
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p. 2357 - 2359
(2007/10/02)
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- NEW APPROACH TO THE USE OF 2-BROMOETHYL ESTERS IN PEPTIDE SYNTHESIS
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The synthesis of six fully protected dipeptides 2-bromoethyl esters and a new method for the removal of the C-protection by the action of the sulphide anion, at room temperature, are described.
- Amaral Trigo, M. Joaquina S. A.,Oliveira Santos, M. Isabel A.
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p. 2787 - 2790
(2007/10/02)
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- Peptides and therapeutic applications thereof
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This invention relates to peptide derivatives of the formula: in which: A is a D.Ala, AzaGly, Aib, D.Ser., D.Thr, D.Cys, homo Serine, βPhe Ser, βOH Leu, 4OH Ile, α,β,γ OHNor Val or OH Val residue in which the side-chain OH or SH groups, when same exist, may be free or protected (i) by a straight- or branched-chain alkyl containing 1-6 carbon atoms, (ii) by an unsubstituted phenyl radical or a phenyl radical substituted with one or more fluorine atoms, (iii) by an unsubstituted benzyl radical or a benzyl radical substituted with one or more fluorine atoms, (iv) by an aliphatic acyl radical having 1-6 carbon atoms or an acyl radical COX in which X is a phenyl, benzyl or benzhydryl radical, optionally substituted with one or more fluorine atoms, B is a L.Phe, pF.L.Phe or pentafluoro L.Phe residue, C is a Leu, N.Leu or Ile residue of D or L configuration, D is hydrogen or a group of the formula: STR1 in which n=0, 1 or 2, R is a hydrogen atom or a radical as defined for the protection of group OH of residue A, Y is a hydrogen atom, a group hydroxy, carboxy, carbamoyl, a group OR1, COOR1 or CONHR1 in which R1 represents a radical as defined for the protection of group OH of residue A, a phosphatidylethanolamine chain or a chain STR2 in which n is an integer from 0 to 3, R2 is a hydrogen atom or a straight alkyl radical containing 1-4 carbon atoms, and R3 is a hydrogen or oxygen atom or a straight alkyl residue containing 1-4 carbon atoms, and their pharmaceutically acceptable salts. Said compounds are therapeutically useful, typically an analgesic, psychotropic and anti-diarrheic agents.
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- On the Double Bond Isostere of the Peptide Bond: Preparation of an Enkephalin Analogue
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Methodology for preparing dipeptide analogues in which a carbon -carbon double bond replaces the normal amide bond is described.Thus, the protected tyrosylglycine analogue, (S)-trans-5-t-butyloxycarbonylamino-6-(4-t-butoxyphenyl)hex-3-enoic acid has been synthesised and incorporated into the Leu-enkephalin analogue (3) by condensation with glycylphenylalanyl-leucine.The enkephalin analogue retained biological activity.The significance of this isosteric replacement of the amide group is discussed.
- Hann, Michael M.,Sammes, Peter G.,Kennewell, Peter D.,Taylor, John B.
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p. 307 - 314
(2007/10/02)
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- Synthesis and biological evaluation of a metazocine-containing enkephalinamide. Evidence for nonidentical roles of the tyramine moiety in opiates and opioid peptides
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In an effort to test the hypothesis that the tyramine moiety present in opiates and in opioid peptides plays an identical functional role at opioid receptors, a hybrid enkephalinamide (3) that contains (-)-metazocine in place of Tyr1 was synthesized. It was found that 3 and its congeners are inactive or feebly active in the electrically stimulated guinea pig ileum and mouse vas deferens preparations. The results of these studies suggest that the tyramine moiety in opiates and related structures does not play the same functional role as that in the opioid peptides. It is suggested that the different functional roles of the tyramine moiety in opiates and opioid peptides is a consequence of different modes of interaction with common receptors.
- Ramakrishnan,Portoghese
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p. 1423 - 1427
(2007/10/02)
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- Lysosomotropic Agents. 4. Carbobenzoxyglycylphenylalanyl, a New Protease-Sensitive Masking Group for Introduction into Cells
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Bioactive primary and secondary amines, when acylated with the Z-Gly-Phe group, are transported into pinocytic cells, such as macrophages, P-815 mastocytoma, SV-40 3T3, and leukemia 1210, much faster than the parent compounds.Amines, such as lysosomotropic detergents and nitrogen mustard, which are deactivated by acylation, are unmasked by enzymic action intracellularly, probably in lysosomes because an acidic pH maximum in activity exists which acts only on the L isomer.The added polarity and molecular weight brought about by acylation prevents the amines' normally facile entry into cells by simple diffusion, restricting it to an active-transport mechanism.
- Firestone, Raymond A.,Pisano, Judith M.,Bailey, Philip J.,Sturm, Anita,Bonney, Robert J.,et al.
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p. 539 - 544
(2007/10/02)
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- Enkaphalin derivatives
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Novel analgesic and antipsychotic agents having the formula STR1 wherein Q is STR2 in which R1 is hydrogen, hydroxy or halogen and R4 is hydrogen or, R1 and R4 are both hydroxy; Z is hydrogen or straight chain lower alkyl having from 1 to 4 carbon atoms and X is methylene, carbonyl, hydroxymethylene, thio, sulfinyl or sulfonyl, or Z and X, taken together, are methylidenyl, with the proviso that when X is sulfonyl or sulfinyl, Z is other than hydrogen; R5 is hydrogen or halogen, and R2 is H, a straight or branched lower alkyl group having from 1 to 4 carbon atoms, the group STR3 or the group STR4 wherein R3 is hydroxy, amino, alkylamino or dialkylamino wherein the alkyl moiety is straight or branched and has from 1 to 4 carbon atoms, diastereomers, enantiomers and pharmaceutically acceptable salts thereof.
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- Evidence of the Preferential Involvement of μ Receptors in Analgesia Using Enkephalins Highly Selective for Peripheral μ or δ Receptors
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In order to study the preferential involvement of μ or δ receptors in the analgesic effects of enkephalins, several peptides which selectively interact with these two kinds of receptors in peripheral organs were synthesized.The inhibitory potency on the e
- Gacel, Gilles,Fournie-Zaluski, Marie-Claude,Fellion, Etienne,Roques, Bernard P.
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p. 1119 - 1124
(2007/10/02)
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