N6-(Retinylidene)lysine

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 597576

CAS#: 34372-62-8

Description: N6-(Retinylidene)lysine is a protein.


Price and Availability

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N6-(Retinylidene)lysine is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 597576
Name: N6-(Retinylidene)lysine
CAS#: 34372-62-8
Chemical Formula: C26H40N2O2
Exact Mass: 412.309
Molecular Weight: 412.61
Elemental Analysis: C, 75.68; H, 9.77; N, 6.79; O, 7.75


Synonym: N6-(Retinylidene)lysine; Nepsilon-All-trans-retinylidene-L-lysine;

IUPAC/Chemical Name: (E)-N6-((2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ylidene)-L-lysine

InChi Key: ITYGDJHCZMOEMH-KWRQVLCYSA-N

InChi Code: InChI=1S/C26H40N2O2/c1-20(14-15-23-22(3)12-9-17-26(23,4)5)10-8-11-21(2)16-19-28-18-7-6-13-24(27)25(29)30/h8,10-11,14-16,19,24H,6-7,9,12-13,17-18,27H2,1-5H3,(H,29,30)/b11-8+,15-14+,20-10+,21-16+,28-19+/t24-/m0/s1

SMILES Code: N[C@@H](CCCC/N=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C)C(O)=O


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>3 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
2934.99.03.00


References

1: Devine EL, Oprian DD, Theobald DL. Relocating the active-site lysine in rhodopsin and implications for evolution of retinylidene proteins. Proc Natl Acad Sci U S A. 2013 Aug 13;110(33):13351-5. doi: 10.1073/pnas.1306826110. Epub 2013 Jul 31. PubMed PMID: 23904486; PubMed Central PMCID: PMC3746867.

2: Li H, Govorunova EG, Sineshchekov OA, Spudich JL. Role of a helix B lysine residue in the photoactive site in channelrhodopsins. Biophys J. 2014 Apr 15;106(8):1607-17. doi: 10.1016/j.bpj.2014.03.002. PubMed PMID: 24739160; PubMed Central PMCID: PMC4008836.

3: Sonar SM, Singh AK. Location of lysine-129 and lysine-40/41 with respect to retinylidene chromophore in bacteriorhodopsin. Biochim Biophys Acta. 1991 Jan 29;1076(2):239-44. PubMed PMID: 1900199.

4: Eilers M, Reeves PJ, Ying W, Khorana HG, Smith SO. Magic angle spinning NMR of the protonated retinylidene Schiff base nitrogen in rhodopsin: expression of 15N-lysine- and 13C-glycine-labeled opsin in a stable cell line. Proc Natl Acad Sci U S A. 1999 Jan 19;96(2):487-92. PubMed PMID: 9892660; PubMed Central PMCID: PMC15163.

5: Devine EL, Theobald DL, Oprian DD. Relocating the Active-Site Lysine in Rhodopsin: 2. Evolutionary Intermediates. Biochemistry. 2016 Aug 30;55(34):4864-70. doi: 10.1021/acs.biochem.6b00478. Epub 2016 Aug 12. PubMed PMID: 27486845; PubMed Central PMCID: PMC5305276.

6: Singh AK, Sandorfy C, Fendler JH. Retinylidene Schiff bases in alkylammonium carboxylate reversed micelles. Biochim Biophys Acta. 1990 Oct 12;1036(1):34-40. PubMed PMID: 2171658.

7: Piechnick R, Heck M, Sommer ME. Alkylated hydroxylamine derivatives eliminate peripheral retinylidene Schiff bases but cannot enter the retinal binding pocket of light-activated rhodopsin. Biochemistry. 2011 Aug 23;50(33):7168-76. doi: 10.1021/bi200675y. Epub 2011 Jul 26. PubMed PMID: 21766795.

8: Argade PV, Rothschild KJ, Kawamoto AH, Herzfeld J, Herlihy WC. Resonance Raman spectroscopy of specifically [epsilon-15N]lysine-labeled bacteriorhodopsin. Proc Natl Acad Sci U S A. 1981 Mar;78(3):1643-6. PubMed PMID: 6785758; PubMed Central PMCID: PMC319188.

9: Matsuyama T, Yamashita T, Imai H, Shichida Y. Covalent bond between ligand and receptor required for efficient activation in rhodopsin. J Biol Chem. 2010 Mar 12;285(11):8114-21. doi: 10.1074/jbc.M109.063875. Epub 2009 Dec 30. PubMed PMID: 20042594; PubMed Central PMCID: PMC2832962.

10: Fischer U, Oesterhelt D. Chromophore equilibria in bacteriorhodopsin. Biophys J. 1979 Nov;28(2):211-30. PubMed PMID: 122264; PubMed Central PMCID: PMC1328626.

11: Akhtar M, Blosse PT, Dewhurst PB. Studies on vision. The nature of the retinal-opsin linkage. Biochem J. 1968 Dec;110(4):693-702. PubMed PMID: 5704817; PubMed Central PMCID: PMC1187442.

12: Schweiger U, Tittor J, Oesterhelt D. Bacteriorhodopsin can function without a covalent linkage between retinal and protein. Biochemistry. 1994 Jan 18;33(2):535-41. PubMed PMID: 8286383.

13: Babu KR, Dukkipati A, Birge RR, Knox BE. Regulation of phototransduction in short-wavelength cone visual pigments via the retinylidene Schiff base counterion. Biochemistry. 2001 Nov 20;40(46):13760-6. PubMed PMID: 11705364.

14: Creemers AF, Kiihne S, Bovee-Geurts PH, DeGrip WJ, Lugtenburg J, de Groot HJ. (1)H and (13)C MAS NMR evidence for pronounced ligand-protein interactions involving the ionone ring of the retinylidene chromophore in rhodopsin. Proc Natl Acad Sci U S A. 2002 Jul 9;99(14):9101-6. Epub 2002 Jul 1. PubMed PMID: 12093898; PubMed Central PMCID: PMC123100.

15: Katre NV, Wolber PK, Stoeckenius W, Stroud RM. Attachment site(s) of retinal in bacteriorhodopsin. Proc Natl Acad Sci U S A. 1981 Jul;78(7):4068-72. PubMed PMID: 6794028; PubMed Central PMCID: PMC319727.

16: Maeda A, Herzfeld J, Belenky M, Needleman R, Gennis RB, Balashov SP, Ebrey TG. Water-mediated hydrogen-bonded network on the cytoplasmic side of the Schiff base of the L photointermediate of bacteriorhodopsin. Biochemistry. 2003 Dec 9;42(48):14122-9. PubMed PMID: 14640679.

17: Gushchin I, Chervakov P, Kuzmichev P, Popov AN, Round E, Borshchevskiy V, Ishchenko A, Petrovskaya L, Chupin V, Dolgikh DA, Arseniev AS, Kirpichnikov M, Gordeliy V. Structural insights into the proton pumping by unusual proteorhodopsin from nonmarine bacteria. Proc Natl Acad Sci U S A. 2013 Jul 30;110(31):12631-6. doi: 10.1073/pnas.1221629110. Epub 2013 Jul 19. Erratum in: Proc Natl Acad Sci U S A. 2013 Sep 3;110(36):14813. Arseniev, Alexander A [corrected to Arseniev, Alexander S]. PubMed PMID: 23872846; PubMed Central PMCID: PMC3732926.

18: Wolber PK, Stoeckenius W. Retinal migration during dark reduction of bacteriorhodopsin. Proc Natl Acad Sci U S A. 1984 Apr;81:2303-7. PubMed PMID: 11541977; PubMed Central PMCID: PMC345047.

19: Han M, Lou J, Nakanishi K, Sakmar TP, Smith SO. Partial agonist activity of 11-cis-retinal in rhodopsin mutants. J Biol Chem. 1997 Sep 12;272(37):23081-5. PubMed PMID: 9287308.

20: Matsumoto H, Yoshizawa T. Rhodopsin regeneration is accelerated via noncovalent 11-cis retinal-opsin complex--a role of retinal binding pocket of opsin. Photochem Photobiol. 2008 Jul-Aug;84(4):985-9. doi: 10.1111/j.1751-1097.2008.00338.x. Epub 2008 Apr 9. PubMed PMID: 18399914.