The Synthesis and Evaluation of Peptide-Based Probes for ...
Peptide Catalog 2017 · 2017. 11. 10. · 1 1. Labeled Peptide Probes for Molecular Imaging 1.1...
Transcript of Peptide Catalog 2017 · 2017. 11. 10. · 1 1. Labeled Peptide Probes for Molecular Imaging 1.1...
PeptideCatalog 2017
4. PEG Modified Peptides........................................................................................................9
5. N-Methyl Modification (Me-Scan).................................................................................... 9
6. MAPs.........................................................................................................................................10
7. Peptide-Protein Conjutates..............................................................................................10
8. Stapled Peptides...................................................................................................................11
9. Cyclic Peptides......................................................................................................................11
10. Peptides’ Phosphorylation............................................................................................12
11. Peptides’ Lipidation..........................................................................................................13
12. Disulfide Formation..........................................................................................................14
13. Thioether Formation.........................................................................................................15
14. Biotinylation.........................................................................................................................15
15. Click Conjugation in Peptide Chemistry..................................................................15
1. Labeled Peptide Probes for Molecular Imaging.........................................................1
1.1 Fluorophore-Labeled Peptide Probes..............................................................................1 1.2 Radio-Labeled Peptide Probes...................................................................................... 3
2. Caspase Inhibitor; Peptidyl CMK, FMK, AOMK and CHO..................................... 4
2.1 Peptidyl CMK...............................................................................................................4
2.2 Peptidyl FMK............................................................................................................... 5
2.3 Peptidyl AOMK............................................................................................................ 5
2.4 Peptidyl Aldehyde.........................................................................................................6
3. Caspase Substrate; Peptidyl AMC, AFC and PNA...................................................7
3.1 Peptidyl AMC...............................................................................................................7
3.2 Peptidyl AFC................................................................................................................7
3.3 Peptidyl PNA................................................................................................................8
Contents
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1. Labeled Peptide Probes for Molecular Imaging
1.1 Fluorophore-labeled Peptide Probes
1.1.1 Alexa Fluor Series
Labeled groupsAbsorptionmaximum
(nm)
Emissionmaximum
(nm)Modification sites
Alexa Fluor 350
Alexa Fluor 405
Alexa Fluor 430
Alexa Fluor 488
Alexa Fluor 514
Alexa Fluor 532
Alexa Fluor 594
N-Terminal, Side Chain of Lys or Cys
N-Terminal, Side Chain of Lys or Cys
N-Terminal, Side Chain of Lys or Cys
N-Terminal, Side Chain of Lys or Cys
N-Terminal, Side Chain of Lys or Cys
N-Terminal, Side Chain of Lys or Cys
N-Terminal, Side Chain of Lys or Cys
346
400
430
494
517
530
590
445
424
545
517
542
555
617
1.1.3 Cy Series
Labeled groupsAbsorptionmaximum
(nm)
Emissionmaximum
(nm)Modification sites
Cy-3
Cy-5
Cy-5.5
Cy-7
N-Terminal, Side Chain of Lys or Cys
N-Terminal, Side Chain of Lys or Cys
N-Terminal, Side Chain of Lys or Cys
N-Terminal, Side Chain of Lys or Cys
550
646
673
747
565
664
692
774
1.1.2 QSY Series
Labeled groupsAbsorptionmaximum
(nm)
Emissionmaximum
(nm)Modification sites
QSY-7
QSY-9
QSY-21
N-Terminal, Side Chain of Lys or Cys
N-Terminal, Side Chain of Lys or Cys
N-Terminal, Side Chain of Lys or Cys
560
562
661
None
None
None
2
1.1.4 Rhodamine Series
1.1.5 Fluorescein Series
Labeled groupsAbsorptionmaximum
(nm)
Emissionmaximum
(nm)Modification sites
FITC
FAM
N-Terminal, Side Chain of Lys or Cys
N-Terminal, Side Chain of Lys or Cys
494
494
518
522
Labeled groupsAbsorptionmaximum
(nm)
Emissionmaximum
(nm)Modification sites
Texas Red
RF488
TAMRA
Rhodamine B
Rhodamine Red-X
N-Terminal, Side Chain of Lys or Cys
N-Terminal, Side Chain of Lys or Cys
N-Terminal, Side Chain of Lys or Cys
N-Terminal, Side Chain of Lys
N-Terminal, and Side Chain of Lys
595
498
565
555
570
615
520
580
580
590
1.1.6 Bodipy Series
Labeled groupsAbsorptionmaximum
(nm)
Emissionmaximum
(nm)Modification sites
Bodipy 493/503
Bodipy FL
Bodipy R6G
Bodipy 530/550
Bodipy TMR-X
Bodipy 558/568
Bodipy 576/589
Bodipy 581/591
Bodipy TR
Bodipy 630/650
N-Terminal, Side Chain of Lys or Cys
N-Terminal, Side Chain of Lys or Cys
N-Terminal, Side Chain of Lys or Cys
N-Terminal, and Side Chain of Lys
N-Terminal, Side Chain of Lys or Cys
N-Terminal, Side Chain of Lys or Cys
N-Terminal, Side Chain of Lys or Cys
N-Terminal, and Side Chain of Lys
N-Terminal, Side Chain of Lys or Cys
N-Terminal, and Side Chain of Lys
500
505
528
534
542
558
576
584
589
625
506
513
550
554
574
569
590
592
617
640
N N
NN
NN
OH N
N
N
NHO
O
O
OH
OOH
HO O
OHO
O
OH
O
OH
O
O
HO
O
OH
O
HO
O
OH
DOTA NOTADTPA
3
1.2 Radio-labeled Peptide Probes
N N
NN
NN
OH N
N
N
NHO
O
O
OH
OOH
HO O
OHO
O
OH
O
OH
O
O
HO
O
OH
O
HO
O
OH
DOTA NOTADTPA
N N
NN
NN
OH N
N
N
NHO
O
O
OH
OOH
HO O
OHO
O
OH
O
OH
O
O
HO
O
OH
O
HO
O
OH
DOTA NOTADTPA
1.1.7 Other Series
Labeled groups Absorptionmaximum
(nm)
Emissionmaximum
(nm)
Modification sites
Dansyl
Dabcyl
DNP
MCA
SBF
EDANS
7-OHCCA
Dacia
N-Terminal, Side Chain of Lys
N-Terminal, Side Chain of Lys
N-Terminal, and Side Chain of Lys
N-Terminal, and Side Chain of Lys
Side Chain of Cys
Side Chain of Glu or Asp
N-Terminal, and Side Chain of Lys
Side Chain of Cys
333
broad
350
358
385 and 515
335
342 (pH=4)
376
518
None
None
69
None
493
447 (pH=4)
465
2. Caspase Inhibitor; Peptidyl CMK, FMK, AOMK and CHO
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2.1 Peptidyl CMK
Cell-permeable, irreversible inhibitor of caspase-1 (ICE). N.Rouquet et al. showed that Ac-YVAD-CMK is a potent therapeutic agent against in vivo liver apoptosis in mice.
Ac-Tyr-Val-Ala-Asp-Chloromethylketone5 mg
25 mg
$ 115
$ 459
Ac-DEVD-CMK irreversibly inhibits caspase-3. It is also active towards caspases-6, -7, -8, and -10.
Ac-Asp-Glu-Val-Asp-Chloromethylketone1 mg
5 mg
$ 31
$ 90
AAF-CMK, serine protease inhibitor. For tripeptidyl peptidase I (E.C. 3.4.14.9) a Ki value of 63 nM has been reported.
H-Ala-Ala-Phe-Chloromethylketone25 mg
100 mg
$ 186
$ 559
Biotinylated analog of the caspase-1 inhibitor YVAD-CMK, N-1330.
Biotinyl-Tyr-Val-Ala-Asp-Chloromethylketone5 mg
25 mg
$ 180
$ 716
Z-YVAD-CMK, inhibitor of caspase-1.
Z-Tyr-Val-Ala-Asp-Chloromethylketone5 mg
25 mg
$ 252
$ 1000
2.2 Peptidyl FMK
2.3 Peptidyl AOMK
5
Methyl ester of Z-DEVD-FMK, a specific caspase-3 inhibitor. Z-D(OMe)E(OMe)VD(OMe)-FMK reduces vulnerability to the neuronal death that occurs in the aftermath of kainic acid-evoked status epilepticus (SE).
Z-Asp(OMe)-Glu(OMe)-Val-Asp(OMe)-Fluoromethylketone1 mg
5 mg
$ 152
$ 610
6-FAM-IE(OMe)TD(OMe)-FMK, the methyl ester of FAM-IETD-FMK, is a cell-permeable, non-toxic inhibitor that binds irreversibly to activated caspase-8 in apoptotic cells. The inhibitor allows to determine the amount of cells present in different stages of the apoptotic cascade and to calculate cell death kinetics. The fluorescence intensity can be measured by flow cytometry, microwell plate reader, or fluorescence microscopy.
Fluorescein-6-carbonyl-Ile-Glu(OMe)-Thr-Asp(OMe)-Fluoromethylketone0.5 mg
1 mg
$ 593
$ 1084
Cell-permeable, irreversible inhibitor of para-caspase MALT1. Z-VRPR-FMK is based on the sequence of a published optimal tetrapeptide substrate for the A. thaliana metacaspase AtMC9.
Z-Val-Arg-Pro-Arg-Fluoromethylketone0.5 mg
1 mg
$ 291
$ 542
Methyl ester of Z-VDVAD-FMK. This cell-permeable fluoromethylketone inhibits specifically caspase-2 and, to a lesser degree, caspase-3 and caspase-7.
Z-Val-Asp(OMe)-Val-Ala-Asp(OMe)-Fluoromethylketone1 mg
5 mg
$ 372
$ 1491
Biotinylated analog of the caspase-1 inhibitor Z-VAD-FMK, N-1510.
Biotinyl-Val-Ala-Asp-fluoromethylketone1 mg
5 mg
$ 711
$ 2881
Ac-YVK(biotinyl)D-AOMK, inhibitor of caspase-1 can affinity label active apoptosis-associated caspase-1 related proteases in cell-free extracts. The substrate preferences of these labeled proteases can be analyzed using cleavage site peptides.
Ac-Tyr-Val-Lys(biotinyl)-Asp-2,6-Dimethylbenzoyloxymethylketone1 mg
5 mg
$ 57
$ 230
Ac-YVAD-AOMK is a highly selective, competitive and irreversible inhibitor of caspase-1 (ICE). Ac-YVAD-AOM inactivates the enzyme with a rate limited by diffusion and is relatively inert toward other bionucleophiles such as glutathione, making it an excellent candidate for in vivo studies of enzyme inhibitors.
Ac-Tyr-Val-Ala-Asp-2,6-dimethylbenzoyloxymethylketone5 mg
25 mg
$ 143
$ 576
2.4 Peptidyl Aldehyde
6
The peptide aldehyde Ac-IETD-CHO corresponds to one of the cleavage sites of the inactive 32 kD caspase-3 precursor (amino acids 172-175). In a concentration range of 0.5 µM, Ac-IETD-CHOblocked the formation of the p17 subunit and concomitantly induced the accumulation of the 32 kD precursor.
Ac-Ile-Glu-Thr-Asp-Aldehyde5 mg
25 mg
$ 143
$ 576
Ac-YVAD-CHO is a potent, specific, reversible inhibitor of caspase-1 (ICE). It displayed a Ki of 0.2 ± 0.1 nM for recombinant human caspase-1.
Ac-Tyr-Val-Ala-Asp-Aldehyde5 mg
25 mg
$ 143
$ 576
The peptide aldehyde Ac-ESMD-CHO corresponds to one of the cleavage sites of the inactive 32 kD caspase-3 precursor (amino acids 25-28). In a concentration range of 2.5 - 5 µM, it blocked the formation of the p17 subunit and concomitantly induced the accumulation of the p20 peptide.
Ac-Glu-Ser-Met-Asp-Aldehyde5 mg
25 mg
$ 143
$ 576
Ac-LEVD-CHO, inhibitor of caspase-4 (ICH-2).
Ac-Leu-Glu-Val-Asp-Aldehyde5 mg
25 mg
$ 143
$ 576
This biotinylated apopain inhibitor has successfully been used for the affinity purification - on a streptavidin-agarose column - of caspase-3 (apopain), the enzyme that cleaves the poly(ADP-ribose) polymerase (PARP). Biotinyl-DE-VD-CHO showed an inhibitory activity comparable to that of the N-acetylated analog inhibitor (H-2496) (IC50 = 0.2 nM).
Biotinyl-Asp-Glu-Val-Asp-Aldehyde5 mg
25 mg
$ 180
$ 711
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3. Caspase Substrate; Peptidyl AMC, AFC and PNA
3.1 Peptidyl AMC
3.2 Peptidyl AFC
Z-LLE-AMC is an excellent fluorogenic substrate for measuring the peptidylglutamyl-peptide-hydrolyzing (PGPH) activity of the 20S proteasome. See also e.g. I-1085 (for assaying the trypsin-like activity) and I-1395 (for determining the chymotrypsin-like activity).
Z-Leu-Leu-Glu-AMC5 mg
25 mg
$ 172
$ 689
Acetyl-KQKLR-AMC, fluorogenic substrate for cathepsin S.
Ac-Lys-Gln-Lys-Leu-Arg-AMC1 mg
5 mg
$ 115
$ 466
Acetyl-KQKLR-AMC, fluorogenic substrate for cathepsin S.
Ac-Phe-Arg-AMC50 mg
250 mg
$ 244
$ 976
Suc-AAV-AMC is cleaved by neprilysin 2.
Suc-Ala-Ala-Val-AMC50 mg
250 mg
$ 477
$ 1922
Z-RLRGG-AMC is a fluorogenic substrate for the deubiquitinating enzyme isopeptidase T (IPaseT) and other ubiqui-tin C-terminal hydrolases (UCHs) based on the C-termini of ubiquitin with a kcat/Km value of 95 M-¹s-¹. Together with our product I-1685 it is used in continuous assays for precise mechanistic studies or microtiter plate assays for high-throughput inhibitor screening.
Z-Arg-Leu-Arg-Gly-Gly-AMC25 mg
100 mg
$ 143
$ 430
The fluorogenic substrate Z-IETD-AFC corresponds to one of the cleavage sites of the inactive 32 kD caspase-3 precursor (amino acids 172-175). Substrate for granzyme B.
Z-Ile-Glu-Thr-Asp-AFC5 mg
25 mg
$ 265
$ 1062
The presence of halogen substituents at the fluorescent group improves membrane permeability of the YVAD-de-rived caspase-1 substrate.
Ac-Tyr-Val-Ala-Asp-AFC5 mg
25 mg
$ 172
$ 689
3.3 Peptidyl PNA
8
Z-VEID-AFC, fluorogenic substrate for caspase-6 (Mch2).
Z-Val-Glu-Ile-Asp-AFC ammonium salt5 mg
25 mg
$ 240
$ 961
Ac-WEHD-AFC, fluorogenic caspase-1 substrate
Ac-Trp-Glu-His-Asp-AFC trifluoroacetate salt10 mg
50 mg
$ 245
$ 867
Z-VEID-AFC, fluorogenic substrate for caspase-6 (Mch2).
Z-Val-Glu-Ile-Asp-AFC5 mg
25 mg
$ 240
$ 961
Ac-AAPF-pNA, chromogenic substrate for chymotrypsin and an excellent substrate for proteinase yscD (saccharoly-sin).
Ac-Ala-Ala-Pro-Phe-PNA50 mg
250 mg
$ 338
$ 1288
The cleavage of the chromogenic caspase-3 substrate Ac-DEVD-pNA can be monitored at 405 nm.
Ac-Asp-Glu-Val-Asp-PNA5 mg
25 mg
$ 72
$ 286
Boc-QAR-pNA, chromogenic substrate for trypsin and matriptase-2.
Boc-Gln-Ala-Arg-PNA50 mg
250 mg
$ 178
$ 717
Suc-AAF-pNA, a sensitive substrate for subtilisins, proteinase K, thermitase, and chymotrypsin.
Suc-Ala-Ala-Phe-PNA250 mg
1000 mg
$501
$1506
Astacin, a zinc-endopeptidase from the crayfish Astacusastacus, hydrolyzes the pentaalanine substrate Suc-AAAAA-pNA at two positions. The first, highly specific cleavage yields Suc-Ala-Ala and Ala-Ala-Ala-pNA (L-1090); the second, much less specific cleavage releases p-nitroaniline from the generated chromogenic substrate.
Suc-Ala-Ala-Ala-Ala-Ala-PNA25 mg
100 mg
$406
$1186
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4. PEG Modified Peptides
H-Pro-PEG4-Cys-Pro-Glu-Thr-Asp-Asp-Arg-Pro-Cys-OH(Cys&Cys disulfide)
10 mg
50 mg
$ 254
$ 1016
PEG2000-Gly-Pro-Gly-Thr-Asp-Thr-Lys-Ala-Tyr-Val-Arg-Asp-Ser-Tyr-Thr-Ala-Leu-Ser-Ser-Ala-Leu-Arg-Pro-Asp-Ile-Val-Gln-Arg-Arg-Phe-Ala-Gly-Ser-Thr-Arg-His-His-Leu-Arg-Lys-Lys-OH
5 mg
25 mg
$ 1016
$ 4237
5. N-Methyl Modification (Me-Scan)
c(RGDf(NMe)V) peptide Cilengitide (EMD 121974; NSC 707544) is a potent integrin inhibitor for αvβ3 and αvβ5 integ-rin with IC50 of 4.1 nM and 79 nM, respectively; ~10-fold selectivity against gpIIbIIIa.
Cyclo(Arg-Gly-Asp-D-Phe-NMe-Val)100 mg
1000 mg
$ 508
$ 1525
Thispeptide is the fragment of Histone H3 (15-39) monomethylated at Lys27 with a C-terminal followed by a biotinylat-ed Lys.
Ala-Pro-Arg-Lys-Gln-Leu-Ala-Thr-Lys-Ala-Ala-Arg-Lys(Me)-Ser-Ala-Pro-Ala-Thr-Gly-Gly-Val-Lys-Lys-Pro-His-Lys(Biotin)-NH2
1 mg
5 mg
$ 180
$ 423
TSRHK-K(Me)-LMFKT peptide is derived from amino acid residues 377-387 of human p53 tumor suppressor protein, with monomethylation at Lys382. Methylation of p53 at Lys382 inhibits expression of p53 target genes and decreases apoptotic and cell cycle arrest functions of p53. This allows p53-dependent DNA repair without apoptosis. Levels of this peptide decrease in response to DNA damage
Thr-Ser-Arg-His-Lys-Lys(Me)-Leu-Met-Phe-Lys-Thr1 mg
5 mg
$ 180
$ 423
Efficient fluorogenic substrate for two matrix metalloproteinases: interstitial collagenase (MMP-1) and gelatinase (MMP-9). Dnp-Pro-Cha-Gly-Cys(Me)-His-Ala-Lys(N-Me-Abz)-amide has favorable solubility characteristics. Both enzymes cleave this substrate between Gly and Cys(Me) (Smc), liberating a cleavage product with a fluorescence signal suitable for inhibitor screening and determining Ki values. The major advantage of this FRET substrate is its adaptability to filters commonly available on commercial plate readers (excitation at 365 nm and emission at 450 nm).
Dnp-Pro-β-cyclohexyl-Ala-Gly-Cys(Me)-His-Ala-Lys(NMe-Abz)-NH25 mg
25 mg
$ 423
$ 813
10
7. Peptide-Protein Conjutates
This linear AVP analog is an extremely high-affinity and selective antagonist at V-1a vasopressin receptors. Conve-nient derivatization of the Lysε-amino group with AMC or biotin leads to highly selective V-1a ligands that are, e.g., useful for receptor localization and purification studies.
Phenylac-D-Tyr(Me)-Phe-Gln-Asn-Arg-Pro-Arg-Lys-NH25 mg
25 mg
$ 254
$ 372
6. MAPs
(RGFAFVTF)8-MAP, multiple antigenic peptide.
(H-Arg-Gly-Phe-Ala-Phe-Val-Thr-Phe)8-MAP1 mg
5 mg
$ 644
$ 2542
Multiple antigenic peptide (KILNDLSSDAPGVPR)8-MAP, the sequence corresponds to rat CREB (136-150).
(H-Lys-Ile-Leu-Asn-Asp-Leu-Ser-Ser-Asp-Ala-Pro-Gly-Val-Pro-Arg)8-MAP1 mg
5 mg
$ 677
$ 2542
(KGLGLKGGLG)4-MAP, multiple antigenic peptide.
(H-Lys-Gly-Leu-Gly-Leu-Lys-Gly-Gly-Leu-Gly)4-MAP25 mg
100 mg
$135
$423
1)KLH (Keyhole Limpet Hemocyanin) 2)BSA (Bovine Serum Albumin) 3)OVA (Ovalbumin)
11
8. Stapled Peptides
9. Cyclic Peptides
An RGD tumor-targeting peptide, which binds to αvβ3 receptors. It can be easily conjugated to fluorophore tags, chelators, or carriers. Palecek et al. converted the ε-amino group into the azide by diazo transfer allowing further functionalization by click chemistry. Mercapto groups can be introduced via acylation of this peptide with S-acetylthio-acetic acid (SATA).
Cyclo(Arg-Gly-Asp-D-Phe-Lys)5 mg
25 mg
$ 254
$ 508
Melanotan II, a cyclic MSH analog, is a potent full agonist of the melanocortin-3 and melanocortin-4 receptors (MC3-R and MC4-R). Intracerebroventricular administration of MTII inhibited feeding in four different mouse models of hyper-phagia. MTII is a valuable tool for the study of the agouti obesity syndrome and of the role of melanocortinergic neurons in feeding.
Ac-Nle-cyclo(-Asp-His-D-Phe-Arg-Trp-Lys)5 mg
25 mg
$ 254
$ 1016
It has been demonstrated that the RGD-containing peptide, c(GRGDSPA), inhibited the binding of fibronectin to stimulated platelets with IC50=0.223 µM. c(GRGDSPA) also blocked thrombin-induced platelet aggregation with IC50= 32 µM, but was less potent than native fibronectin in this respect.
Cyclo(Gly-Arg-Gly-Asp-Ser-Pro-Ala)5 mg
25 mg
$ 508
$ 847
This sulfur-bridged cyclopeptide is a potent inhibitor of the binding of glycoprotein IIb/IIIa to fibrinogen with an IC50 of 1.5 nM. Furthermore, it is a highly potent inhibitor of fibrinogen-mediated platelet aggregation (IC50= 0.15 µM). Its antithrombotic activity in vivo may render this compound useful in the treatment of arterial thromboembolic diseases.
Cyclo(-D-Tyr-Arg-Gly-Asp-Cys(carboxymethyl)-OH) sulfoxide1 mg
5 mg
$ 161
$ 644
Somatostatin antagonist.
Cyclo(7-aminoheptanoyl-Phe-D-Trp-Lys-Thr(Bzl))5 mg
25 mg
$ 355
$ 1389
FITC-betaAla-Glu-Ile-Trp-Leu-Ala-Gln-Glu-Leu-Arg-S5-Ile-Gly-Asp-R8-Phe-Asn-Ala-Tyr-Tyr-Ala Stapled between S5 &R8)
1 mg
5 mg
$ 644
$ 2542
12
10. Peptides’ Phosphorylation
WFYpSPR-pNA, chromogenic substrate for Pin1, an essential and conserved mitotic peptidyl-prolyl isomerase (PPIase), that specifically recognizes the phosphoserine-proline bonds present in mitotic phosphoproteins.
H-Trp-Phe-Tyr-Ser(PO3H2)-Pro-Arg-pNA1 mg
5 mg
$ 135
$ 542
A protein tyrosine phosphatases substrate. The use of this phosphopeptide substrate is highly recommended for the detection and characterization of a wide variety of intracellular and receptor-linked protein tyrosine phosphatases, particularly when limiting amounts of tissue extracts or immunoprecipitates are concerned.
H-Glu-Asn-Asp-Tyr(PO3H2)-Ile-Asn-Ala-Ser-Leu-OH1 mg
5 mg
$ 250
$ 1000
The phosphopeptide EPQ(p)YEEIPIYL is derived from the hamster polyoma middle-T antigen. It binds with high affinity and specificity to the Src homology-2 (SH2) domains of the protein tyrosine kinases p56 lck and p60 src. The side chains of residues pY (phosphotyrosine) and Ile at position pY+3 were shown to occupy deep binding pockets of either SH2 domain surface.
H-Glu-Pro-Gln-Tyr(PO3H2)-Glu-Glu-Ile-Pro-Ile-Tyr-Leu-OH1 mg
5 mg
$ 254
$ 1016
The small mammalian heat shock proteins show a highly conserved amino acid sequence and are suggested to play a major role in the increased thermal resistance acquired by cells after exposure to heat shock. They possess two major sites of phosphorylation which are each located in the conserved protein kinase phosphorylation site motif Arg-X-X-Ser. The above-mentioned phosphopeptide, which contains the second site of phosphorylation, has been isolated from a tryptic digest of phosphorylated native and recombinant mouse hsp 25. Only Ser86, the first of the three serine residues, is phosphorylated
H-Cys-Leu-Asn-Arg-Gln-Leu-Ser(PO3H2)-Ser-Gly-Val-Ser-Glu-Ile-Arg-OH1 mg
5 mg
$ 305
$ 1220
This peptide corresponds to residues 317 to 320 of the oncogenic protein Shc. Similar phosphotyrosine motifs are also found in receptor tyrosine kinases and substrates of them. This peptide binds with high affinity (18 nM) to the SH2 domain of the growth factor bound-2 protein (Grb2). It is a useful inhibitor of the interaction of Grb2 with Shc, or with other Grb-2-binding proteins involved in the cell signaling cascade.
H-Tyr(PO3H2)-Val-Asn-Val-OH1 mg
5 mg
$ 237
$ 949
11. Peptides’ Lipidation
13
The non-toxic lipopeptide Pam3CSKKKK is a highly effective adjuvant for parenteral, oral and nasal immunizations. It readily dissolves in aqueous solvents and might also be applicable for DNA immunizations.
Palmitoyl-Cys((RS)-2, 3-di(palmitoyloxy)-propyl)-Ser-Lys-Lys-Lys-Lys-OH5 mg
25 mg
$ 762
$ 3050
The synthetic lipopeptide analog Pam3Cys-Ala-Gly, which corresponds to the N-terminal region of a bacterial lipopro-tein, is a potent activator of macrophages. It is suggested that the uptake of Pam3CAG into macrophages involves the aggregation of membrane proteins.
Palmitoyl-Cys((RS)-2, 3-di(palmitoyloxy)-propyl)-Ala-Gly-OH5 mg
25 mg
$ 254
$ 1016
The myristylated pentapeptide Myr-KRTLR is an effective inhibitor of the protein kinase C (PKC)-catalyzed histone phosphorylation (inhibitory constant, IC50 = 75 µM). It competes with the phosphoacceptor substrate of PKC and interacts with the phospholipid cofactor of the enzyme.
Myristoyl-Lys-Arg-Thr-Leu-Arg-OH5 mg
25 mg
$ 69
$ 271
The myristoylated nonapeptide Myr-FARKGALRQ corresponding to the pseudosubstrate domain of PKC-α and -β subtypes represents a selective and cell-permeable inhibitor of PKC in intact cells.
Myristoyl-Phe-Ala-Arg-Lys-Gly-Ala-Leu-Arg-Gln-OH5 mg
25 mg
$ 228
$ 847
Ghrelin, a peptide hormone produced by the stomach oxyntic cells plays a crucial role in appetite regulation. It binds to the growth hormone secretagogue receptor (GHS-R), which stimulates the release of GH. Ghrelin, which promotes food uptake and body weight increase, acts as an antagonist of leptin. Thus, it has become an important tool in obesi-ty research.Additionally, ghrelin is involved in the bone metabolism, in reproduction, and in the immune system.
H-Gly-Ser-Ser(octanoyl)-Phe-Leu-Ser-Pro-Glu-His-Gln-Lys-Ala-Gln-Gln-Arg-Lys-Glu-Ser-Lys-Lys-Pro-Pro-Ala-Lys-Leu-Gln-Pro-Arg-OH
1 mg
5 mg
$ 491
$ 2033
12. Disulfide Formation
14
Potent vasoconstrictor that acts on endothelia cells and on the underlying smooth muscle cells as a modulator of vascular tone. ET-1 displays selectivity for ETA receptor.
Cys-Ser-Cys-Ser-Ser-Leu-Met-Asp-Lys-Glu-Cys-Val-Tyr-Phe-Cys-His-Leu-Asp-Ile-Ile-Trp(Cys1&Cys15 Bridge, Cys3&Cys11 Bridge)(Endothelin-1)
1 mg
5 mg
$ 203
$ 847
This peptide displays a higher contractor activity on mouse and guinea pig, whereas it is weaker in its vasoconstric-tor activity.
Cys-Ser-Cys-Asn-Ser-Trp-Leu-Asp-Lys-Glu-Cys-Val-Tyr-Phe-Cys-His-Leu-Asp-Ile-Ile-Trp(Cys1&Cys15Bridge, Cys3&Cys11Bridge)(VasiactuveIntest-inalContractor)
1 mg
5 mg
$ 203
$ 847
Relaxin H2 is the major stored and circulating isoform of the peptide hormone relaxin in humans. This pregnancy hormone has also shown cardioprotective activity. The observed long-term effects of relaxin H2 on connective tissues may be due to alterations in the turnover of collagen and proteoglycans.
(Pyr-Leu-Tyr-Ser-Ala-Leu-Ala-Asn-Lys-Cys-Cys-His-Val-Gly-Cys-Thr-Lys-Arg-Ser-Leu-Ala-Arg-Phe-Cys-OH)A(H-Asp-Ser-Trp-Met-Glu-Glu-Val-Ile-Lys-Leu-Cys-Gly-Arg-Glu-Leu-Val-Arg-Ala-Gln-Ile-Ala-Ile-Cys-Gly-Met-Ser-Thr-Trp-Ser-OH)B (Cys10A&Cys15A Bridge, Cys11A&Cys11B Bridge, Cys24A &Cys23B Bridge) (Relaxin H2 Human)
1 mg
5 mg
$ 1355
$ 5423
Relaxin H2 is the major stored and circulating isoform of the peptide hormone relaxin in humans. This pregnancy hormone has also shown cardioprotective activity. The observed long-term effects of relaxin H2 on connective tissues may be due to alterations in the turnover of collagen and proteoglycans.
(H-Asp-Val-Leu-Ala-Gly-Leu-Ser-Ser-Ser-Cys-Cys-Lys-Trp-Gly-Cys-Ser-Lys-Ser-Glu-Ile-Ser-Ser-Leu-Cys-OH)A(H-Arg-Ala-Ala-Pro-Tyr-Gly-Val-Arg-Leu-Cys-Gly-Arg-Glu-Phe-Ile-Arg-Ala-Val-Ile-Phe-Thr-Cys-Gly-Gly-Ser-Arg-Trp-OH)B (Cys10&Cys15 Bridge A, Cys11A&Cys10B Bridge, Cys24A &Cys22B Bridge) (Relaxin H3 Human)
1 mg
5 mg
$ 1355
$ 5423
This peptide acts as substrate for the disulfide bond-forming enzymes protein disulfide-isomerase (PDI) and DsbA (a periplasmic protein thiol:disulfide oxidoreductase). NRCSQGSCWN permits the rapid determination of the pH-depen-dence of the activity of both enzymes.
H-Asn-Arg-Cys-Ser-Gln-Gly-Ser-Cys-Trp-Asn-OH (Disulfide bond)5 mg
25 mg
$ 254
$ 847
13. Thioether Formation
14. Biotinylation
15. Click Conjugation in Peptide Chemistry
15
(Biotinyl-ACTH (1-39) (human))
Biotinyl-Ser-Tyr-Ser-Met-Glu-His-Phe-Arg-Trp-Gly-Lys-Pro-Val-Gly-Lys-Lys-Arg-Arg-Pro-Val-Lys-Val-Tyr-Pro-Asn-Gly-Ala-Glu-Asp-Glu-Ser-Ala-Glu-Ala-Phe-Pro-Leu-Glu-Phe-OH
1 mg
5 mg
$ 128
$ 508
(Biotinyl-pTH (1-34) (human)
Biotinyl-Ser-Val-Ser-Glu-Ile-Gln-Leu-Met-His-Asn-Leu-Gly-Lys-His-Leu-Asn-Ser-Met-Glu-Arg-Val-Glu-Trp-Leu-Arg-Lys-Lys-Leu-Gln-Asp-Val-His-Asn-Phe-OH trifluoroacetate salt
5 mg
25 mg
$ 203
$ 593
GLP-1 (7-36)-Lys(biotinyl) amide (human, bovine, guinea pig, mouse, rat)
H-His-Ala-Glu-Gly-Thr-Phe-Thr-Ser-Asp-Val-Ser-Ser-Tyr-Leu-Glu-Gly-Gln-Ala-Ala-Lys-Glu-Phe-Ile-Ala-Trp-Leu-Val-Lys-Gly-Arg-Lys(biotinyl)-NH2
1 mg
5 mg
$ 423
$ 1694
This biotinylated ω-conotoxin GVIA is a useful ligand for the characterization of calcium channels
Biotinyl-εAhx-Cys-Lys-Ser-Hyp-Gly-Ser-Ser-Cys-Ser-Hyp-Thr-Ser-Tyr-Asn-Cys-Cys-Arg-Ser-Cys-Asn-Hyp-Tyr-Thr-Lys-Arg-Cys-Tyr-NH2(Cys2 & Cys17 Bridge, Cys9 & Cys20, Cys16 & Cys27 Bridge)
1 mg
5 mg
$ 430
$ 1694
Biotinyl-α-CGRP (human) trifluoroacetate salt
Biotinyl-Ala-Cys-Asp-Thr-Ala-Thr-Cys-Val-Thr-His-Arg-Leu-Ala-Gly-Leu-Leu-Ser-Arg-Ser-Gly-Gly-Val-Val-Lys-Asn-Asn-Phe-Val-Pro-Thr-Asn-Val-Gly-Ser-Lys-Ala-Phe-NH2 trifluoroacetate salt (Disulfide bond)
1 mg
5 mg
$ 1322
$ 5084
Cyclo(C4-Tyr-Leu-Asp-Gly-Cys-Pro-Ile-Ala) (C4&Cys Side Chain ThioesterBridge)
5 mg
20 mg
$ 338
$ 1694
Ala-Tyr-Ile-Gln-Asn-HomoCys-Pro-Lys-Gly-NH2
(Ala&HomoCys Side Chain ThioesterBridge)5 mg
20 mg
$ 5000
$ 3389
Zhejiang Ontores Biotechnologies Co.,Ltd
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2017001 2017. 4