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1.
Carlos García-Echeverría 《Letters in Peptide Science》1995,2(2):93-98
Summary A series of peptides related to some of the autophosphorylation sites of the epidermal growth factor receptor has been synthesized on solid phase, using side-chain-unprotected phosphotyrosine. Although the desired peptides could be obtained, this approach was not entirely satisfactory due to a side reaction that gave the pyrophosphate derivative of the target peptide. Under identical coupling conditions, the extension of this side reaction appears to be sequence dependent.Abbreviations BOP
benzotriazolyloxy-tris-(dimethylamino)phosphonium hexafluorophosphate
- DCM
dichloromethane
- DIEA
diisopropylethylamine
- EGF
epidermal growth factor
- EGFR
epidermal growth factor receptor
- FABMS
fast atom bombardment mass spectrometry
- Fmoc
fluorenylmethoxycarbonyl
- HATU
N-[(dimethylamino)1H-1,2,3-triazolo[4,5-b]pyridin-1-ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide
- HOBt
1-hydroxybenzotriazole
- HPLC
high-performance liquid chromatography
- MALDI-TOF
matrix-assisted laser-desorption ionization time-of-flight mass spectrometry
- MBHA
4-methylbenzhydrylamine resin
- PAL
tris(alkoxy)benzylamide linker
- PEG
polyethylene glycol
- TFA
trifluoroacetic acid
- TPTU
2-(2-pyridon-1-yl)-1,1,3,3-tetramethyluroniumfluoroborate
- tR
retention time
Abbreviations used for amino acids follow the recommendations of the IUPAC-IUB Commission of Biochemical Nomenclature [Eur. J. Biochem., 138 (1984) 9]. 相似文献
2.
Camarero Julio A. Adeva Alberto Muir Tom W. 《International journal of peptide research and therapeutics》2000,7(1):17-21
Summary This paper describes a practical new use of 3-mercaptopropionic acid as a highly versatile multidetachable linker for solid-phase
synthesis. Our approach is based on the stability of the alkylthioester functionality to optimized Boc-SPPS protocols and
HF treatment, as well as on the mild activation of the thioester functionality toward nucleophilic or reductive displacement.
This allows several C-terminal modifications to be introduced into a synthetic molecule during the cleavage step. We have
shown that unprotected peptides can be efficiently cleaved from a propyl thioester-polyethylene glycol-poly-(N,N-dimethylacrylamide) copolymer resin using a great variety of nucleophiles to give the corresponding C-terminally modified
peptides (esters, thioesters, carboxylic acids, thioacids, amides, hydroxamic acids, hydrazides, alcohols). The nucleophilic
cleavage reaction is both rapid and exceptionally clean in all the cases tested.
Abbreviations: HBTU,N-[(1H-benzotriazol-1-yl)(dimethylamino)methylene]-N-methylmethanaminium hexafluorophosphateN-oxide); DIEA,N,N-diisopropylethylamine; DMF,N,N-dimethyl formamide; ES-MS, electrospray mass spectrometry; FAB-MS, fast atom bombardment mass spectrometry; HMBA, hydroxymethylbenzoic
acid; HPLC, high performance liquid chromatography; PBS: phosphate buffer saline; PEGA, polyethylene glycolpoly-(N,N-dimethylacrylamide); TFA, trifluoroacetic acid; SPPS, solid-phase peptide synthesis. Standard IUPAC single and triple letter
codes for amino acids are used throughout 相似文献
3.
Nokihara Kiyoshi Nagawa Yoshinobu Hong Seon-Pyo Nakanishi Hiroshi 《International journal of peptide research and therapeutics》1997,4(3):141-146
Summary Peptide chain assembly is now routinely performed by the use of automated synthesizers, although purification and characterization
of large peptides still requires knowledge and experience. Structural biology has recently become closely involved in molecular
recognition studies that often require the analysis of relatively large peptides using high-resolution NMR spectroscopy, for
which synthesis of high-quality peptides in 5–10 mg amounts is of prime importance. The present study describes a solid-phase
synthesis of a 7 kDa peptide related to the recently characterized ethylene-responsive element binding protein of tobacco,
which is the conserved sequence among these proteins. The rapid and efficient preparation was carried out through a single
coupling in combination with a single HPLC separation step. Assembly was performed in 63 h. Different coupling chemistries
were employed and compared, involving benzotriazol-1-yloxy-tris(pyrrolidino)phosphonium hexafluorophosphate, 1-hydroxy-7-azabenzotriazole
and/or the recently introduced reagent,N-[(dimethylamino)-1H-1,2,3-triazolo[4,5-b]pyridin-1-ylmethylene]-N-methylmethanaminium hexafluorophosphateN-oxide. After each synthesis, purified material was characterized by mass spectrometry, sequencing and enzymatic mapping and
shown to contain a high proportion of the desired peptide. 相似文献
4.
García-Echeverría Carlos Stamm Christelle Wille Roman Arz Dorothee Gay Brigitte 《International journal of peptide research and therapeutics》1997,4(1):49-53
Summary A series of biotinylated phosphopeptides has been synthesized and used in the development of an ELISA-based approach to assess
SH2/PTB-phosphoprotein interactions in vitro in terms of affinity and specificity.
Abbreviations: BSA, bovine serum albumin; DMSO, dimethylsulfoxie; EGF, epidermal growth factor; ELISA, enzyme-linked immunosorbent assay;
HATU,N-[(dimethylamino)1H-1,2,3-triazolo[4,5-b]pyridin-1-ylmethylene]-N-methylmethan-aminium hexafluorophosphateN-oxide; HPLC, high-performance liquid chromatography; GST, glutathione-S-transferase; pY, phosphotyrosine; TFA, trifluoroacetic acid; Tris, tris(hydroxymethyl)aminomethane; TBS-T, Tris buffered
saline Tween. The abbreviations used for amino acids follow the recommendations of the IUPAC-IUB Commission of Biochemical
Nomenclature [Eur. J. Biochem., 138 (1984) 9]. 相似文献
5.
Carlos García-Echeverría 《Letters in Peptide Science》1996,2(6):369-373
Summary In order to minimise the formation of the pyrophosphate derivative of the target peptide when side-chain-unprotected phopshotyrosine is used in solid-phase peptide synthesis, this building block can be incorporated using benzotriazolyloxy-tris-(dimethylamino)phosphonium hexafluorophosphate/1-hydroxybenzotriazole/N-methylmorpholine (1:1:2.3) in the presence of a chaotropic salt (0.4 M LiCl in N-methyl-2-pyrrolidinone).Abbreviations BOP
benzotriazolyloxy-tris-(dimethylamino)phosphonium hexafluorophosphate
- DIEA
diisopropylethylamine
- Fmoc
9-fluorenylmethoxycarbony
- HATU
N-[(dimethylamino)1H-1,2,3-triazolo[4,5-b]pyridin-1-ylmethylene]-N-methylmethan-aminium hexafluorophosphate N-oxide
- HOBt
1-hydroxybenzotriazole
- HPLC
high-performance liquid chromatography
- MALDI-TOF
matrix-assisted laser-desorption ionization time-of-flight mass spectrometry
- NMM
N-methylmorpholine
- NMP
N-methyl-2-pyrrolidinone
- Pmc
2,2,5,7,8-pentamethyl-chroman-6-sulfonyl
- ®
solid support
- TFA
trifluoroacetic acid
- TPTU
2-(2-pyridon-1-yl)-1,1,3,3-tetramethyluroniumfluoroborate. Abbreviations used for amino acids follow the recommendations of the IUPAC-IUB Commission of Biochemical Nomenclature [Eur. J. Biochem., 138 (1984) 9] 相似文献
6.
Summary Oxytocin, a nonapeptide amide, was synthesized on a PEGA-resin using the Fmoc-tBu strategy. The sulfhydryl groups of the two cysteine residues were protected with trityl groups. Different oxidation reagents such as DMSO, I2 and thallium (III) trifluoroacetate mixed with TFA were evaluated in order to obtain oxytocin in a one-pot reaction. The mixture of TFA and DMSO (5:1) in which oxytocin was formed quantitatively was found to be the optimal method. The cyclic oxytocin could be isolated in 56% yield.Abbreviations Acm
acetamidomethyl
- DCM
dichloromethane
- Dhbt
3,4-dihydro-4-oxobenzotriazin-3-yl
- DMF
dimethylformamide
- DMSO
dimethylsulfoxide
- Fmoc
9-fluorenylmethyloxycarbonyl
- MALDI
matrix-assisted laser desorption ionisation
- NEM
4-ethylmorpholine
- PEGA
polyethylene glycol-poly-N,N-dimethylacrylamide co-polymer
- Pfp
pentafluorophenyl
- TBTU
O-(1H-benzotriazol-1-yl)-N,N,N,N-tetramethyluronium tetrafluoroborate
-
tBu
tert-butyl
- TFA
trifluoroacetic acid
- TIS
triisopropylsilane
- Tl(tfa)3
thallium(III) trifluoroacetate; Trt, triphenylmethyl 相似文献
7.
Summary Two series of intramolecularly quenched fluorogenic oligopeptide substrates with the general sequences DABCYL-Lys-Phe-Gly-Gly-Ala-Xxx-EDANS and Abz-Lys-Phe-Gly-Gly-Ala-Xxx-Tyr(m-NO2)-NH2 have been used to explore the effect of P3 substituents and donor/acceptor pairs on the kinetic parameters for papain-catalyzed hydrolysis. The steady-state constants are moderately affected by amino acid or fluorophore/quencher replacement. No correlation between the hydrophobicity of the P3 substituent and the kinetic parameters was found.Abbreviations Abz
anthranilic acid or anthranilamide
- Boc
tert-butyloxycarbonyl
- BOP
benzotriazolyloxy tris-(dimethylamino)-phosphonium hexafluorophosphate
- DABCYL
4-(4-dimethylaminophenylazo)benzoic acid
- DCM
dichloro-methane
- DIEA
diisopropylethylamine
- DIPCDI
diisopropylcarbodiimide
- DMF
N,N-dimethylformamide
- DMSO
dimethylsulfoxide
- E-64
trans-epoxysuccinyl-l-leucylamido(4-guanidino)butane
- EDCI
1-(3-dimethylaminopropyl)-3-ethylcarbodi-imide hydrochloride
- EDTA
ethylenediaminetetraacetic acid
- EDANS
5-[(2-aminoethyl)amino]naphthalene-1-sulfonic acid
- FABMS
fast atom bombardment mass spectrometry
- Fmoc
9-fluorenylmethyloxycarbonyl
- HOBt
1-hydroxybenzotriazole
- HPLC
high pressure liquid chromatography
- MBHA
4-methylbenzhydrylamine (resin)
- MCA
methylcoumarylamide
- Nle
norleucine
- PAL
tris(alkoxy)benzylamide linker
- Su
succinimide
- TFA
trifluoroacetic acid
- tR
retention time
- Tyr(m-NO2)
meta-nitrotyrosine
- Z
benzyloxycarbonyl
Abbreviations used for amino acids follow the recommendations of the IUPAC-IUB Commission of Biochemical Nomenclature [Eur. J. Biochem., 138 (1984) 9]. Amino acid symbols denote the l-configuration. 相似文献
8.
John W. Perich 《Letters in Peptide Science》1996,3(3):127-132
Summary A novel method for the efficient synthesis of Tyr(P)-containing peptides is described by the phosphite-triester phosphorylation of the tyrosine residue after its incorporation into the peptide chain. In this approach, the peptide resin is assembled by Fmoc solid-phase peptide synthesis (PyBOP® couplings) with the tyrosine residue incorporated as Fmoc-Tyr-OH. The N-terminal tyrosine peptide resin is then phosphorylated with di-t-butylN,N-diethylphosphoramidite/1H-tetrazole and the intermediate di-t-butyl phosphite triester is oxidised by treatment withm-chloroperoxybenzoic acid. Peptide synthesis is then continued under usual conditions and the peptide resin is deprotected by acidolytic treatment. The improved efficiency of the on-line phosphorylation approach is demonstrated through the syntheses of IVPNY(P)VEE and the Fc receptor peptide, EAENTITY(P)SLLKHPEAL, in both good yield and purity.Abbreviations Boc
tert-butyloxycarbonyl
-
t-Bu
tert-butyl
- DCM
dichloromethane
- DMF
dimethylformamide
- FAB-MS
fastatom-bombardment mass spectrometry
- Fmoc
fluorenylmethoxycarbonyl
- HOBt
1-hydroxybenzotriazole
- HMP
hydroxymethylphenoxy
- RP-HPLC
reverse-phase high-performance liquid chromatography
- MALDI
matrix-assisted laser desorption ionisation
- MCPBA
m-chloroperoxybenzoic acid
- NMR
nuclear magnetic resonance
- PyBOP®
1H-benzotriazole-1-yl-oxy-tris(pyrrolidino)-phosphonium hexafluorophosphate
- TFA
trifluoroacetic acid
- Tyr(P)
O-phosphotyrosine
This work was presented at the 21st Annual Lorne Conference on Protein Structure and Function, Lorne, Australia, 4–8 February 1996. 相似文献
9.
Jiménez Jose C. Bayó Nuria Chavarría Bibiana López-Macià Àngel Royo Miriam Nicolás Ernesto Giralt Ernest Albericio Fernando 《International journal of peptide research and therapeutics》2002,9(2-3):135-141
Summary α, β-Didehydroamino acids, which are key components of both natural andde novo peptides, are frequently encountered in naturally occurring peptides — mostly of microbial and fungal origin and/or from
marine organisms. Herein, we report on a reappraisal of the use of the water-soluble carbodiimide/CuCl method for the preparation
of this kind of peptide in both solution and solid-phase modes and describe some side reactions encountered during the process.
Abbreviations: Alloc, allyloxycarbonyl; Barlos resin, 2-chlorotrityl chloride resin, Boc,tert-butoxycarbonyl; Boc2O, di-tert-butyl dicarbonate; Bzl, benzyl; DABCO, 1,4-diazabicyclo[2.2.2]octane; DAST, (diethylamino)sulfur trifluoride; DBU, 1,8-diazabicyclo[5.4.0]undec-7-ene;
DDAAs, α, β-didehydroarnino acids; DEAD, diethyl azodicarboxylate; Dha, Didehydroalanine, (Z)-Dhb, Z-Didebydroaminobutyric
acid; (Z)-Dhp, Z-Didehydrophenylalanine; DSC, disuccinimidyl carbonate; DDP, α, β-didehydropeptides; EDC, WSC, 3-(3′-dimethylaminopropyl)-1-ethylearbodiimide;
Fmoc, fiuorenylmethoxycarbonyl; HATU, N-{(dimethylamino)-1H-1,2,3-triazolo[4,5-b]pyridino-1-ylmethylene}-N-methylmethanaminium
hexafluorophosphate; HOAt, 1-hydroxy-7-azabenzotriazole; (β-OH)Phe, phenylserine or β-hydroxyphenylalanine; Ph3P, triphenylphosphine; PyAOP, (7-azabenzotriazol-1-yloxy)-tris(pyrrolidino)phosphonium hexafluorophosphate; TEA, triethylamine;
TFA, trifluoroacetic acid. Amino acid symbols denote thel-configuration unless stated otherwise. All solvent ratios are volume/volume unless stated otherwise. 相似文献
10.
G. Gaus M. Casaretto H. Stieve 《Journal of comparative physiology. B, Biochemical, systemic, and environmental physiology》1994,164(3):191-194
Four neuropeptides have been isolated and sequenced from acetone extracts of brains of the horseshoe crab Limulus polyphemus. They belong to a newly discovered peptide family in invertebrates. A possible role of the four peptides from Limulus as cardioregulatory neurotransmitters has been tested on the isolated Limulus heart. Three of the peptides (DEGHKMLYFamide, GHSLLHFamide, and PDHHMMYFamide) produce dose-dependent decreases in both amplitude and rate of the heart contractions, whereas DHGNMLYFamide reduces only the amplitude of the heartbeat. All four peptides differ in threshold, potency and duration of their effects.Abbreviations DIC
diisopropylcarbodiimide
- DTT
dithiotreitol
- Fmoc
9-fluorenylmethyloxycarbonyl
- GABA
gamma amino butyric acid
- HOBt
N-hydroxybenzotriazole
- HPLC
high performance liquid chromatography
- IBMX
3-isobutyl 1-methyl-xanthine
- Lip-HP
Limulus head peptide
- LP
Limulus peptide
- TBTU
2-(1H-benzotriazole-1yl)-1,1,3,3,tetramethyluronium tetrafluoroborate
- TFA
trifluoroacetic acid
- TLC
thin-layer chromatography 相似文献
11.
R. M. Valerio A. M. Bray N. J. Maeji P. O. Morgan J. W. Perich 《Letters in Peptide Science》1995,2(1):33-40
Summary The synthesis of two model Tyr(P)-containing peptides using Fmoc-Tyr(PO3
tBu2)-OH, Fmoc-Tyr(PO3Bzl2)-OH and Fmoc-Tyr(PO3H2)-OH established that the t-butylphosphate-protected derivative was the preferred derivative for use in Fmoc solid-phase peptide synthesis, since it afforded phosphopeptides in high purity and with the lowest amount of Tyr-peptide contamination. In addition, this study confirmed that commercially available Fmoc-Tyr(PO3H2)-OH is also suitable for use in Fmoc solid-phase synthesis but gives less pure phosphopeptides, along with the generation of 1–4% of the tyrosine-containing peptide for the model sequences studied. In view of the good performance of Fmoc-Tyr(PO3
tBu2)-OH, a large-scale three-step synthetic procedure was developed which involved phenacyl protection of the carboxyl group, phosphite-triester phosphorylation of the tyrosyl hydroxyl using di-t-butyl N,N-diethylphosphoramidite, and final removal of the phenacyl group by zinc reduction in acetic acid.Abbreviations BOP
benzotriazol-1-yl-oxy-tris(dimethylamino)phosphonium hexafluorophosphate
-
tBu
t-butyl
- Bzl
benzyl
- DBU
1,8-diazabicyclo[5,4,0]undec-7-ene
- DMF
N,N-dimethylformamide
- EDT
ethanedithiol
- Fmoc
9-fluorenylmethoxycarbonyl
- HOBt
N-hydroxybenzotriazole
- HPLC
high performance liquid chromatography
- NMM
N-methylmorpholine
- Pac
phenacyl
- TFA
trifluoroacetic acid
- THF
tetrahydrofuran
- Tyr(P)
O-phosphotyrosine 相似文献
12.
Summary A convenient method for the synthesis of symmetric and asymmetric diamides of amino acids including DOPA and citric acid from 2-tert-butyl-1,3-di(N-hydroxysuccinimidyl)citrate and 1-tert-butyl-2,3-di(N-hydroxysuccinimidyl)citrate is described.Abbreviations AcOtBu
tert-butyl acetate
- i-Bu
iso-butyl
-
tBu
tert-butyl
- Bzl
benzyl
- p-OH-Bzl
p-hydroxybenzyl
- m,p-(OH)2-Bzl
m,p-dihydroxybenzyl
- DCCI
dicyclohexylcarbodiimide
- Et
ethyl
- Me
methyl
- Su
succinimidyl
- SuOH
N-hydroxysuccinimide
- Ph
phenyl 相似文献
13.
Summary Mixtures of cyclic peptides, formed by head-to-tail cyclizations of side-chain resin-bound linear sequences, have been prepared using solid-phase synthesis. Fast atom bombardment mass spectrometry of cyclic peptides with various metal ions can reveal preferred modes of host-guest patterns, albeit in a nonquantitative manner. This approach could prove useful for more rapid screening of potential peptide ionophores. A cyclic heptapeptide with a dipeptide tail proved to be a particularly effective host for a Ca2+ ion; in a small three-component mixture, cyclo[Gly-Asp-d-Pro-Xxx-Asp-d-Pro-Asp(Aca-Phe-NH2)], binding to Ca2+ varied from Xxx=N-MeAla>GlySar. In a 15-component mixture, cyclo[Pro-Xxx-Asn-Pro-Xxx-Asn] where Xxx=Ala, Glu, Leu, Lys or Phe, there were no significant differences with respect to binding to metal ions. We believe this to be the first reported use of cyclic peptide libraries for screening metal ions to discern host-guest relationships.Abbreviations Aca
aminocaproic acid
- Boc
tert-butyloxycarbonyl
- BOP
benzotriazolyloxy-tris(dimethylamino)phosphonium hexafluorophosphate
- DCM
dichloromethane
- DIEA
diisopropylethylamine
- DMF
N,N-dimethylformamide
- ESI
electrospray ionization
- FABMS
fast atom bombardment mass spectrometry
- pMBHA
4-methylbenzhydrylamine
- TFA
trifluoroacetic acid
This paper is based on a presentation given at the Symposium on Peptide Structure and Design as part of the 31st Annual ACS Western Regional Meeting held in San Diego, CA, USA, October 18–21, 1995. 相似文献
14.
Gomez-Martinez Paloma Guibé François Albericio Fernando 《International journal of peptide research and therapeutics》2000,7(4):187-194
Summary The solid-phase synthesis of peptides containing Cys has been carried out using the new thiol protecting group Fsam, which
is completely stable to basic and acidic conditions used in both main strategies and can be selectively removed by palladium-catalyzed
allylic cleavage in the presence of nucleophiles. This protecting group adds a new dimension of orthogonality for regioselective
cysteine pairing strategies.
Abbreviations: Those used for amino acids and the designations of peptides follow the rules of the IUPAC-IUB Commission of Biochemical Nomenclature
inJ. Biol. Chem.
1972,247, 977–983. The following additional abbreviations are used: Acm,S-acetamidomethyl; Alloc, allyloxycarbonyl; BME, β-mercaptoethanol; Boc,tert-butyloxycarbonyl; Bu, butyl;tBu,tert-butyl; Bzl, benzyl; DIEA,N,N-diisopropylethylamine; DIP-CDI,N,N′-diisopropylcarbodiimide; DMF,N,N-dimethylformamide; EtOAc, ethyl acetate; Fm, fluorenylmethyl; Fmoc, fluorenylmethyloxycarbonyl; Fmoc-AM,p-[(R,S)-α-[1-(9HFluoren-9-yl)methoxyformamido]-2,4-dimethoxybenzyl]-phenoxyacetic acid; Fnam,S-[N-[2,3,5,6-tetrafluoro-4-(N′-piperidino)-phenyl],N-allyloxycarbonyl]-aminomethyl Fsam,S-[N-[2,3,5,6-tetrafluoro-4-(phenylthio)-phenyl],N-allyloxycarbonyl]-aminomethyl; HOAc, acetic acid; HOBt, 1-hydroxybenzotriazole; Meb,S-4-methylbenzyl; Mmt,S-4-methoxytriphenylmethyl; Mob,S-4-methoxybenzyl; NDMBA,N,N′-dimethylbarbituric acid; Npys,S-3-nitro-2-pyridinesulfenyl; OPac, phenacyl ester; PEG-PS, poly(ethyleneglycol)-polystyrene graft resin support; Ph, phenyl;
Phacm,S-phenylacetamidomethyl; StBu,S-tert-butylmercapto; SPPS, solid-phase peptide synthesis; TFA, trifluoroacetic acid; THF, tetrahydrofuran; Tmob,S-2,4,6-trimethoxybenzyl; Trt,S-triphenylmethyl. Amino acid symbols denote the L-configuration unless indicated otherwise. 相似文献
15.
A. A. Morozova N. V. Sumbatyan V. P. Lezina V. Kh. Akparov G. A. Korshunova T. A. Gudasheva 《Russian Journal of Bioorganic Chemistry》2008,34(5):550-562
Cyclic peptides cyclo(-Gly-Asp-Glu-Lys-), cyclo(-Gly-Gly-Asp-Glu-Lys-) and cyclo(-Gly-Gly-Gly-Asp-Glu-Lys-) were synthesized as models of theβ-turn of nerve growth factor loop 4. The corresponding protected linear precursors were obtained in 52–83% yields by the solid-phase method with the use of the Fmoc/Bu t strategy and a chlorotrityl anchor group. The cyclization was carried out with benzotriazolyloxytris(dimethylamino)phosphonium (BOP) hexafluorophosphate, N-[(1H-benzotriazole-1-yl)-(dimethylamino)methylene]-N-methylmetanaminium-N-oxide (HBTU) hexafluorophosphate, and diphenylphosphorylazide (DPPA) at a dilution of 10?3 M. The distribution of reaction products was studied for each cyclopeptide in dependence on the type of the coupling agent. The use of DPPA was shown to completely inhibit the formation of cyclodimers in the synthesis of five-and six-membered cyclopeptides; however, in the case of a four-membered peptide, an additional tenfold dilution of the reaction mixture was necessary to achieve the effect. The identification of several byproducts during the synthesis showed that the elongation of the polypeptide chain using the BOP reagent can be complicated by substantial racemization, and the cleavage of the chlorotrityl anchor group by 0.5% TFA in dichloromethane proceeds with insufficient selectivity and is accompanied by the premature Boc deblocking of the lysine side function. 相似文献
16.
We demonstrate that 9-amino-NeuAc transferred to asialo-1-acid glycoprotein resists cleavage by bacterial, viral and mammalian sialidases. This is the first synthetic sialic acid analogue, which can be activated and transferred to glycoprotein, but is not a sialidase (EC 3.2.1.18) substrate.Abbreviations HPLC
high performance liquid chromatography
- BSA
bovine serum albumin
- NeuAc
N-acetyl-d-neuraminic acid, 5-acetamido-3,5-dideoxy-d-glycero-d-galacto-non-2-ulosonic acid
- 9-Amino-NeuAc
9-amino-5-N-acetyl-d-neuraminic acid, 5-acetamido-9-trideoxy-d-glycero-d-galacto-non-2-ulosonic acid
- CMP-NeuAc
cytidine-5-monophospho-N-acetyl-d-neuraminic acid
- CMP-9-amino-NeuAc
cytidine-5-monophospho-9-amino-5-N-acetyl-d-neuraminic acid
- 9-azido-NeuAc
5-acetamido-9-azido-3,5,9-trideoxy-d-glycero-d-galacto-non-2-ulosonic acid.
Enzymes EC 3.2.1.18
sialidase, acylneuraminylhydrolase
- EC 2.4.99.1
Galß1-4GlcNAc a(2-6)-sialytransferase 相似文献
17.
Dr. Patrick R. Meffre 《Amino acids》1999,16(3-4):251-272
Summary Strategies for the synthesis of optically active aspartaldehyde derivatives are reviewed. Most of them are using the chiral pool: allylglycine or naturally occurring homoserine, aspartic acid or methionme and side chain modifications. This will be developed in the first part. Some other original routes are also displayed in the second part. Different aspects of each strategy are discussed: the nature and number of steps, the problem of protecting groups, the price and availability of starting materials. Some synthetic applications of such interesting chiral synthons are shown in the last part.Abbreviations Ac
acetyl
- An
Anisyl or 4-methoxy benzyl
- Bn
benzyl
- Boc
tert-butoxycarbonyl
- BOP-PF6
benzotriazol-l-yloxytris(dimethylamino)phosphonium hexafluorophosphate
- Cbz
benzyloxycarbonyl
- DCC
dicyclohexylcarbodiimide
- DIBAL
diisobutyl aluminum hydride
- DIPEA
diisopropyl ethyl amine
- DMF
dimethyl formamide
- DMSO
dimethylsulfoxide
- EDCI
l-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride
- HP
4-hydroxy phenyl
- MP
4-methoxy phenyl
- NCS
N-chlorosuccinimide
- NMR
nuclear magnetic resonance
- PCC
pyridinium chlorochromate
- Pht
phthaloyl
- Ser
serine
-
tBu
tert-butyl
- TEMPO
2,2,6,6-tetramethyl piperidine-l-oxyl
- TFA
trifluoro acetic acid
- Trityl
triphenyl methyl
- Val
valine
This paper is dedicated to RV. 相似文献
18.
Summary
N--peptidyl-l-lysine p-nitroanilides may easily be prepared under mild conditions starting from commercially available H-Lys(Boc)-pNA (3) and N--tritylated amino acids using CF3-PyBOP (1) as condensating reagent. An illustration of this approach was given by the synthesis of the novel promising plasmin substrate isovaleryl-l-phenylalanyl-l-lysine p-nitroanilide hydrochloride (6).Abbreviations Boc
t-butyloxycarbonyl
- CF3-PyBOP
[6-(trifluoromethyl)benzotriazol-l-yloxy]tris(pyrrolidino)phosphonium hexafluorophosphate
- DEA
diethylamine
- DIEA
N,N-diisopropylethylamine
- Fmoc
fluoren-9-yl-methoxycarbonyl
- Isoval
isovaleryl
- pNA
p-nitroanilide
- Trt
trityl
- Z
benzyloxycarbonyl 相似文献
19.
N-Fluorenylmethyloxycarbonyl-protected serine and threonine derivatives, carryingO-glycosidically - or -linked peracetylated -d-Galp-(1–3)-d-GalNAcp carbohydrate chains, were prepared. These derivatives are intended for use in solid phase glycopeptide synthesis. Suitably protected mono- and disaccharide thioglycosides were used as carbohydrate intermediates. These were activated by treatment with bromine to give the glycosyl bromides, which were then used in silver triflate-promoted glycosidations ofN-fluorenylmethyloxycarbonyl amino-acid phenacyl esters. Removal of the phenacyl esters with zinc gave the target free acids. 相似文献
20.
Khattab Sh. N. El-Faham A. El-Massry A. M. Mansour E. M. E. Abd El-Rahman M. M. 《International journal of peptide research and therapeutics》2000,7(6):331-345
Summary The IR studies for the preactivation step of N-protected iminodiacetic acid with different coupling reagents (TCFH, TFFH,
HATU, HBTU, HSTU) were reported here and showed the formation of an anhydride as an active intermediate in case of TCFH and
TFFH. The formation of a mixture of an anhydride and an active ester (-OBt,-OAt or-OSu) were observed for HBTU, HATU or HSTU
coupling reagent. Dependent on the coupling conditions, acylation of N-protected iminodiacetic acid with amino acid ester
or amide derivatives in solution phase gave monoor di-substituted iminodiacetic acid derivatives. Coupling of N-protected
iminodiacetic acid with an amino acid or peptide attached to a solid support (PAL-PEG-PS or Wang resin) gave only the monosubstituted
iminodiacetic acid derivatives.
Abbreviations: HBTU, N-[(1H-benzotriazol-1-yl)(dimethylamino)methylene]-N-methylmethanaminium hexafluorophosphate N-oxide; Boc,t-butyloxycarbonyl; DCC, N,N′-dicyclohexylcarbodiimide; DIC, N,N′-diisopropylcarbodiimide; DIEA, diisopropylethylamine; HATU,
N-[(dimethylamino)-1H-1,2,3,-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate N-oxide; DMF,
N,N-dimethylformamide; Bsmoc, 1,1-dioxobenzo[b]thiophene-2-ylmethoxycarbonyl; Fmoc, 9-fluorenylmethyloxycarbonyl; HOAt, l-hydroxy-7-azabenzotriazole;
HOBt, l-hydroxybenzotriazol; IDA, iminodiacetic acid; HSTU, O-(succinimidyl)-tetramethyluronium hexafluorophosphate; TCFH;
1,1,3,3-tetramethyl-2-chloroformamidinium hexafluorophosphate; TFFH, 1,1,3,3-tetramethyl-2-fluoroformamidinium hexafluorophosphate;
TMS-Cl, trimethylchlorosilane. Amino acids and peptides are abbreviated and designated following the rules of the IUPAC-IUB
Commission of Biochemical Nomenclature (J. Biol. Chem., 247 (1972) 997). 相似文献