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Ala-Asp

Ala-Gln

Ala-lle

Ala-Met

Ala-Val

Asp-Ala

Asp-Gln

Asp-Gly

Glu-Ala

Gly-Asn

Gly-Asp

Gly-lle

His-Ala

His-Glu

His-His

Ile-Asn

Ile-Leu

Leu-Asn

Leu-His

Leu-Pro

Leu-Tyr

Lys-Asp

Lys-Gly

Lys-Met

Met-Thr

Met-Tyr

Phe-Asp

Phe-Glu

Gln-Glu

Phe-Met

Phe-Tyr

Phe-Val

Pro-Arg

Pro-Asn

Pro-Glu

Pro-lle

Pro-Lys

Pro-Ser

Pro-Trp

Pro-Val

Ser-Asn

Ser-Asp

Ser-Gln

Ser-Glu

Thr-Asp

Thr-Gln

Thr-Phe

Thr-Ser

Trp-Val

Tyr-lle

Tyr-Val

Val-Ala

Val-Gln

Val-Glu

Val-Lys

Val-Met

Val-Phe

Val-Pro

Val-Ser

beta-Ala-Ala

beta-Ala-Gly

beta-Ala-His

Met-beta-Ala

beta-Ala-Phe

D-Ala-D-Ala

D-Ala-Gly

D-Ala-Leu

D-Leu-D-Leu

D-Leu-Gly

D-Leu-Tyr

gamma-Glu-Gly

gamma-D-Glu-Gly

Gly-D-Ala

Gly-D-Asp

Gly-D-Ser

Gly-D-Thr

Gly-D-Val

Leu-beta-Ala

Leu-D-Leu

Phe-beta-Ala

Ala-Ala-Ala

D-Ala-Gly-Gly

Gly-Gly-Ala

Gly-Gly-D-Leu

Gly-Gly-Gly

Gly-Gly-lle

Gly-Gly-Leu

Gly-Gly-Phe

Val-Tyr-Val

Gly-Phe-Phe

Leu-Gly-Gly

Leu-Leu-Leu

Phe-Gly-Gly

Tyr-Gly-Gly

Leu-Ser

Leu-Trp

Leu-Val

Lys-Ala

Lys-Arg

Lys-Glu

Lys-Ile

Lys-Leu

Lys-Lys

Lys-Phe

Lys-Pro

Lys-Ser

Lys-Thr

Lys-Trp

Lys-Tyr

Lys-Val

Met-Arg

Met-Asp

Met-Gln

Met-Glu

Met-Gly

Met-His

Met-Ile

Met-Leu

Met-Lys

Met-Met

Met-Phe

Met-Pro

Met-Trp

Met-Val

Phe-Ala

Phe-Gly

Phe-Ile

Phe-Phe

Phe-Pro

Phe-Ser

Phe-Trp

Pro-Ala

Pro-Asp

Pro-Gln

Pro-Gly

Pro-Hyp

Pro-Leu

Pro-Phe

Pro-Pro

Pro-Tyr

Ser-Ala

Ser-Gly

Ser-His

Ser-Leu

Ser-Met

Ser-Phe

Ser-Pro

Ser-Ser

Ser-Tyr

Ser-Val

Thr-Ala

Thr-Arg

Thr-Glu

Thr-Gly

Thr-Leu

Thr-Met

Thr-Pro

Trp-Ala

Trp-Arg

Trp-Asp

Trp-Glu

Trp-Gly

Trp-Leu

Trp-Lys

Trp-Phe

Trp-Ser

Trp-Trp

Trp-Tyr

Tyr-Ala

Tyr-Gln

Tyr-Glu

Tyr-Gly

Tyr-His

Tyr-Leu

Tyr-Lys

Tyr-Phe

Tyr-Trp

Tyr-Tyr

Val-Arg

Val-Asn

Val-Asp

Val-Gly

Val-His

Val-Ile

Val-Leu

Val-Tyr

Val-Val

gamma-Glu-Gly

Ala-Ala

Ala-Arg

Ala-Asn

Ala-Glu

Ala-Gly

Ala-His

Ala-Leu

Ala-Lys

Ala-Phe

Ala-Pro

Ala-Ser

Ala-Thr

Ala-Trp

Ala-Tyr

Arg-Ala

Arg-Arg

Arg-Asp

Arg-Gln

Arg-Glu

Arg-Ile

Arg-Leu

Arg-Lys

Arg-Met

Arg-Phe

Arg-Ser

Arg-Trp

Arg-Tyr

Arg-Val

Asn-Glu

Asn-Val

Asp-Asp

Asp-Glu

Asp-Leu

Asp-Lys

Asp-Phe

Asp-Trp

Asp-Val

Cys-Gly

Gln-Gln

Gln-Gly

Glu-Asp

Glu-Glu

Glu-Gly

Glu-Ser

Glu-Trp

Glu-Tyr

Glu-Val

Gly-Ala

Gly-Arg

Gly-Cys

Gly-Gly

Gly-His

Gly-Leu

Gly-Lys

Gly-Met

Gly-Phe

Gly-Pro

Gly-Ser

Gly-Thr

Gly-Trp

Gly-Tyr

Gly-Val

His-Asp

His-Gly

His-Leu

His-Lys

His-Met

His-Pro

His-Ser

His-Trp

His-Tyr

His-Val

Ile-Ala

Ile-Arg

Ile-Gln

Ile-Gly

Ile-His

Ile-Ile

Ile-Met

Ile-Phe

Ile-Pro

Ile-Ser

lle-Trp

Ile-Tyr

Ile-Val

Leu-Ala

Leu-Arg

Leu-Asp

Leu-Glu

Leu-Gly

Leu-Ile

Leu-Leu

Leu-Met

Leu-Phe

Peptide Nitrogen Sources

Synthetic Dipeptides -  A New Dimension in Clinical Nutrition

Prof.Peter Fürst, MD, PhD.
Institute of Biological Chemistry and Nutrition, University of Hohenheim, Stuttgart /Germany.


Dipeptide utilization - human studies
Human studies in healthy volunteers demonstrated that the synthetic glutamine dipeptides L-glutamine (Ala-Gln, present in Dipeptiven®) and glycyl-L-glutamine (Gly-Gin, Present in Glamin®) as well as the synthetic tyrosine dipeptide glycyl-L-tyrosine (Gly-Tyr, present in Glamin®) are rapidly hydrolyzed after bolus injection (elimination half lives 3., 7.8, and 3.8 min, respectively). Continuous infusion of a commercial amino acid solution supplemented with Ala-Gln or Gly-Gln was not accompanied by any side effects, and no complaints were reported. Infusion of peptide-supplemented solutions resulted in a prompt increase in alanine, glutamine, tyrosine and glycine concentrations. During the entire infusion period, only trace amounts of the dipeptides of the dipeptides could be measured in plasma. Urinary losses of dipeptids were only approximately 1% of the given dose. These results indicate a near-quantitative hydrolysis of the infused peptide, with subsequent utilization of the constituent free amino acids.

Phenylalanine and tyrosine metabolism in renal failure: Dipeptides as tyrosine source

Druml, Wilfried; Roth, Erich; Lenz, Kurt; Lochs, Herbert; Kopsa, Herbert, Kidney International Supplement;Nov1989, Issue 27, p282


Oral tyrosine supplementation was shown to replete plasma and intracellular pools and improve nitrogen balance in chronic renal failure patients on a low protein diet. However, because of poor solubility in aqueous solutions, tyrosine cannot be included in the free form in amino acid solutions for parenteral nutrition. To circumvent stability or solubility problems, tyrosine containing dipeptides and/or N-acetyl-tyrosine may serve as tyrosine sources for parenteral supply. Renal failure does not affect alanyl-tyrosine hydrolysis, and there is an immediate increase of plasma tyrosine concentration after peptide infusion. Elimination and hydrolysis of glycine-tyrosine is retarded in renal failure, but the clearance exceeds clinically relevant infusion rates. After infusion of N-acetyl-tyrosine, no increase in plasma tyrosine is seen, and the half-life N-acetyl-tyrosine is grossly prolonged in uremia. Thus, alanyl-tyrosine and glycyl-tyrosine. but not N-acetyl-tyrosine, are excellent tyrosine sources for parenteral nutrition. For the first time, the use of dipeptides permits adequate tyrosine supplementation for uremic patients on parenteral nutritional support.


Angiotensin converting enzyme inhibitory peptides from a lactotripeptide-enriched milk beverage are absorbed intact into the circulation.

Foltz M1, Meynen EE, Bianco V, van Platerink C, Koning TM, Kloek J. ,J Nutr. 2007 Apr;137(4):953-8.


Food products containing angiotensin converting enzyme (ACE) inhibitory peptides reportedly play a role in treatment of mild hypertension. The aim of this placebo-controlled crossover study was to assess the bioavailability of Ile-Pro-Pro and 7 other ACE-inhibiting peptides present in a lactotripeptide (LTP)-enriched yogurt beverage and whether meal intake affects Ile-Pro-Pro bioavailability.  Meal intake affected Ile-Pro-Pro concentrations. When the beverage was consumed after a meal, the AUC of Ile-Pro-Pro was 1.3-fold (P < 0.05) of the AUC derived from premeal intake. This was due to an increase in the plasma elimination half-life (P < 0.05); C(max) and T(max) were not affected by meal intake. In summary, this is the first demonstration, to our knowledge, that the tripeptide Ile-Pro-Pro selectively escapes from intestinal degradation and reaches the circulation undegraded.

Lactotripeptides

are two naturally occurring milk peptides: Isoleucine-Proline-Proline (IPP) and Valine-Proline-Proline (VPP). These lactotripeptides are derived from casein, which is a milk protein also found in dairy products. Although most normal dairy products contain lactotripeptides, they are inactive within the original milk proteins. Dairy peptides can be effectively released through enzymatic predigestion – a process by which milk protein is enzymatically broken down into smaller pieces.

Discovery of Salt Taste Enhancing Arginyl Dipeptides in Protein Digests and Fermented Fish Sauces by Means of a Sensomics Approach

A Schindler et al. J Agric Food Chem 59 (23), 12578-12588. 2011 Nov 14.


Salt Taste Enhancing L-Arginyl Dipeptides From Casein and Lysozyme Released by Peptidases of Basidiomycota

L Harth et al. J Agric Food Chem. 2016 Aug 24.


A Series of Kokumi Peptides Impart the Long-Lasting Mouthfulness of Matured Gouda Cheese

S Toelstede et al. J Agric Food Chem 57 (4), 1440-1448. 2009 Feb 25.


Abstract

Among the gamma-L-glutamyl peptides, the candidates gamma-Glu-Glu, gamma-Glu-Gly, gamma-Glu-Gln, gamma-Glu-Met, gamma-Glu-Leu, and gamma-Glu-His, present in GC44 in concentrations between 4.11 and 17.66 micromol/kg, were identified for the first time as the key kokumi molecules enhancing mouthfulness and complex taste continuity of the matured cheese.


A total of 10 kokumi peptides were identified from yeast extract. They were γ-Glu-Cys-Gly, γ-Glu-Leu, γ-Glu-Val, γ-Glu-Tyr, Leu-Lys, Leu-Gln, Leu-Ala, Leu-Glu, Leu-Thr and Ala-Leu. Apart from the well-known kokumi-active glutathione and γ-glutamyl dipeptides, five leucyl dipeptides were first proposed having kokumi activity. Among them, Ala-Leu was found to have the highest kokumi threshold concentration .

Alteration of the Substrate Specificity of L-Amino Acid Ligase and Selective Synthesis of Met-Gly as a Salt Taste Enhancer

H Kino et al. Biosci Biotechnol Biochem 79 (11), 1827-1832. 2015 Jun 19.

Effective Production of Pro-Gly by Mutagenesis of L-Amino Acid Ligase

H Kino et al. J Biosci Bioeng 122 (2), 155-159. 2016 Mar 24.

Abstract

l-Amino acid ligase (Lal) catalyzes dipeptide synthesis from unprotected l-amino acids by hydrolysis ATP to ADP. Each Lal displays unique substrate specificity, and many different dipeptides can be synthesized by selecting suitable Lal. We have already successfully synthesized Met-Gly selectively by replacing the Pro85 residues of Lal from Bacillus licheniformis (BL00235).

Nutriceuticals

Verwendung von tryptophanhaltigen Peptiden mit blutdrucksenkender und vasoprotektiver Wirkung für die Herstellung  biofunktioneller Lebensmittel.


Molkenproteinhydrolysat mit ACE-hemmender und antihypertensiver Wirkung enthält eine physiologisch wirksame Menge mindestens eines der bioaktiven Dipeptide Ile-Trp und Trp-Leu .


Die Herstellung der damit angereicherten Molkenproteinhydrolysate (whey protein)  ist zugänglich  durch extensive Hydrolyse von Molkenproteinisolaten bzw. reinem α-Lactalbumin.


Ebenso besteht außerdem die Möglichkeit, die Herstellung  von Nahrungsergänzungsmitteln und Nahrungsprodukten, durch definierte Zugabe synthetisch hergestellter Dipeptide  nach eigener Rezeptur zu realisieren.


References

SATO,M.,et.al.: Angiotensin I-Converting Enzyme Inhibitory Peptides Derived from Wakame (Undaria pinnatifida) and Their Anthiypertensive Effect in Spontaneously Hypertensive Rats.In: American Chemical Society,2002,50,S.6245-6252

KUBA,Megumi,et.al.: Angiotensin I-Converting Enzyme Inhibitory Peptides Isolated from Tofuyo Fermented Soybean Food. In: Biosci. Biotechnol.Biochem.67,6,2003,S.1278-1283

MULLALLY,Margaret M.,et.al.: Synthetic Peptides Corresponding to a-lactalbumin and ß-Lactoglobulin Sequences with Angiotensin-I-Converting Enzyme Inhibitory Activity. In: Biol.Chem.Hoppe-Seyler ,Vol.377,S.259-260,April 1996
BIOSIS Abstracts Prev.20000134824

Sequence, taste and umami-enhancing effect of the peptides separated from soy sauce.

Zhuang M1, Lin L2, Zhao M2, Dong Y1, Sun-Waterhouse D2, Chen H1, Qiu C3, Su G4., Food Chem. 2016 Sep 1;206:174-81.

Five tasty peptides were separated from soy sauce, by sensory-guided fractionation, using macroporous resin, medium-pressure liquid chromatography and reverse phase-high performance liquid chromatography, and identified by ultra-performance liquid chromatography tandem mass-spectrometry as ALPEEV, LPEEV, AQALQAQA, EQQQQ and EAGIQ. LPEEV, AQALQAQA and EQQQQ tasted umami with threshold values of 0.43, 1.25 and 0.76mmol/l, respectively. ALPEEV and EAGIQ had minimal umami taste, but ALPEEV, EAGIQ and LPEEV showed umami-enhancement with a threshold estimated at 1.52, 1.94 and 3.41mmol/l, respectively. In addition, the synthetic peptides showed much better sensory taste than mixtures of their constitutive amino acids. It indicated that peptides might play an important role in the umami taste of soy sauce.


Reference:

Pal-ghk peptides Cas No 147732-56-7

Woundhealing peptides

https://books.google.de/books?id=D2a-CgAAQBAJ&pg=PA312&lpg=PA312&dq=pal-ghk+peptide&source=bl&ots=nnluugV0tQ&sig=mpprfqQI7HV3XsuL8cvreuYdwEs&hl=de&sa=X&redir_esc=y#v=onepage&q=pal-ghk%20peptide&f=false


Tyr-Arg = Kyotorphine, analgesic effects



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References

Asp-Glu-Ser : Sour, Salty

… I Assume That The Addition Of Kokumi Peptides To Foods May Help Reduce Fat Intake And Artificial Addition Of Sugars …
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