Bacteriopheophytin
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Hodoodo CAT#: H556134

CAS#: 17453-58-6

Description: Bacteriopheophytin, also known as Bacteriopheophytin a, is a Pigment which is the degradation product of bacteriochlorophyll.


Chemical Structure

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Bacteriopheophytin
CAS# 17453-58-6

Theoretical Analysis

Hodoodo Cat#: H556134
Name: Bacteriopheophytin
CAS#: 17453-58-6
Chemical Formula: C55H76N4O6
Exact Mass: 888.5765
Molecular Weight: 889.235
Elemental Analysis: C, 74.29; H, 8.62; N, 6.30; O, 10.80

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @hodoodo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Bacteriopheophytin; Bacteriopheophytin A;

IUPAC/Chemical Name: methyl (3R,11R,12R,21S,22S)-16-acetyl-11-ethyl-12,17,21,26-tetramethyl-4-oxo-22-[3-oxo-3-[(E,7R,11R)-3,7,11,15-tetramethylhexadec-2-enoxy]propyl]-7,23,24,25-tetrazahexacyclo[18.2.1.15,8.110,13.115,18.02,6]hexacosa-1(23),2(6),5(26),8,10(25),13,15,17,19-nonaene-3-carboxylate

InChi Key: KWOZSBGNAHVCKG-SZQBJALDSA-N

InChi Code: InChI=1S/C55H76N4O6/c1-13-39-34(7)41-29-46-48(38(11)60)36(9)43(57-46)27-42-35(8)40(52(58-42)50-51(55(63)64-12)54(62)49-37(10)44(59-53(49)50)28-45(39)56-41)23-24-47(61)65-26-25-33(6)22-16-21-32(5)20-15-19-31(4)18-14-17-30(2)3/h25,27-32,34-35,39-40,51,57,59H,13-24,26H2,1-12H3/b33-25+,41-29-,42-27-,43-27-,44-28-,45-28-,46-29-,52-50-/t31-,32-,34-,35+,39-,40+,51-/m1/s1

SMILES Code: O=C([C@@H](C1=O)C2=C(N/3)C1=C(C)C3=C\C([C@H](CC)[C@H]/4C)=NC4=C/C5=C(C(C)=O)C(C)=C(N5)/C=C6[C@@H](C)[C@H](CCC(OC/C=C(C)/CCC[C@H](C)CCC[C@H](C)CCCC(C)C)=O)C2=N/6)OC

Appearance: To be determined

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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

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

HS Tariff Code: 2934.99.9001

Instruction:

Preparing Stock Solutions

The following data is based on the product molecular weight 889.235 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Takashima Y, Saga Y. Isomerization kinetics of bacteriochlorophyll b and bacteriopheophytin b under acidic conditions. Photochem Photobiol Sci. 2022 Jul;21(7):1193-1199. doi: 10.1007/s43630-022-00207-1. Epub 2022 Mar 29. PMID: 35349123.

2: Pan J, Saer R, Lin S, Beatty JT, Woodbury NW. Electron Transfer in Bacterial Reaction Centers with the Photoactive Bacteriopheophytin Replaced by a Bacteriochlorophyll through Coordinating Ligand Substitution. Biochemistry. 2016 Sep 6;55(35):4909-18. doi: 10.1021/acs.biochem.6b00317. Epub 2016 Aug 22. PMID: 27478991.

3: Białek R, Burdziński G, Jones MR, Gibasiewicz K. Bacteriopheophytin triplet state in Rhodobacter sphaeroides reaction centers. Photosynth Res. 2016 Aug;129(2):205-16. doi: 10.1007/s11120-016-0290-6. Epub 2016 Jul 1. PMID: 27368166; PMCID: PMC4935742.

4: Mizoguchi T, Isaji M, Harada J, Tsukatani Y, Tamiaki H. The 17-propionate esterifying variants of bacteriochlorophyll-a and bacteriopheophytin-a in purple photosynthetic bacteria. J Photochem Photobiol B. 2015 Jan;142:244-9. doi: 10.1016/j.jphotobiol.2014.12.013. Epub 2014 Dec 19. PMID: 25559490.

5: Saga Y, Ishitani A, Takahashi N, Kawamura K. Production of bacteriopurpurin-18 phytyl ester from bacteriopheophytin a via allomerization by contact with titanium oxides in the presence of molecular oxygen. Bioorg Med Chem Lett. 2015 Feb 1;25(3):639-41. doi: 10.1016/j.bmcl.2014.12.002. Epub 2014 Dec 8. PMID: 25529741.

6: Zhu J, van Stokkum IH, Paparelli L, Jones MR, Groot ML. Early bacteriopheophytin reduction in charge separation in reaction centers of Rhodobacter sphaeroides. Biophys J. 2013 Jun 4;104(11):2493-502. doi: 10.1016/j.bpj.2013.04.026. PMID: 23746522; PMCID: PMC3672893.

7: Pan J, Saer RG, Lin S, Guo Z, Beatty JT, Woodbury NW. The protein environment of the bacteriopheophytin anion modulates charge separation and charge recombination in bacterial reaction centers. J Phys Chem B. 2013 Jun 20;117(24):7179-89. doi: 10.1021/jp400132k. Epub 2013 Jun 10. PMID: 23688348.

8: Sai Sankar Gupta KB, Alia A, Buda F, de Groot HJ, Matysik J. Bacteriopheophytin a in the active branch of the reaction center of rhodobacter sphaeroides is not disturbed by the protein matrix as shown by 13C photo-CIDNP MAS NMR. J Phys Chem B. 2013 Mar 28;117(12):3287-97. doi: 10.1021/jp3121319. Epub 2013 Mar 18. PMID: 23452037.

9: Zabelin AA, Shkuropatova VA, Shuvalov VA, Shkuropatov AY. FTIR spectroscopy of the reaction center of Chloroflexus aurantiacus: photoreduction of the bacteriopheophytin electron acceptor. Biochim Biophys Acta. 2011 Sep;1807(9):1013-21. doi: 10.1016/j.bbabio.2011.05.018. Epub 2011 May 27. PMID: 21641333.

10: Egorova-Zachernyuk T, van Rossum B, Erkelens C, de Groot H. Characterisation of uniformly 13C, 15N labelled bacteriochlorophyll a and bacteriopheophytin a in solution and in solid state: complete assignment of the 13C, 1H and 15N chemical shifts. Magn Reson Chem. 2008 Nov;46(11):1074-83. doi: 10.1002/mrc.2295. PMID: 18802970.

11: Zeng X, Wu Y, Shen Y, Xu C. Replacement of bacteriopheophytin in reaction centers from Rhodobacter sphaeroides RS601 with plant pheophytin. Sci China C Life Sci. 2000 Feb;43(1):21-9. doi: 10.1007/BF02881714. PMID: 18763112.

12: Chuang JI, Boxer SG, Holten D, Kirmaier C. Temperature dependence of electron transfer to the M-side bacteriopheophytin in rhodobacter capsulatus reaction centers. J Phys Chem B. 2008 May 1;112(17):5487-99. doi: 10.1021/jp800082m. Epub 2008 Apr 11. PMID: 18402487.

13: Chuang JI, Boxer SG, Holten D, Kirmaier C. High yield of M-side electron transfer in mutants of Rhodobacter capsulatus reaction centers lacking the L-side bacteriopheophytin. Biochemistry. 2006 Mar 28;45(12):3845-51. doi: 10.1021/bi0601048. PMID: 16548512.

14: Watson AJ, Fyfe PK, Frolov D, Wakeham MC, Nabedryk E, van Grondelle R, Breton J, Jones MR. Replacement or exclusion of the B-branch bacteriopheophytin in the purple bacterial reaction centre: the H(B) cofactor is not required for assembly or core function of the Rhodobacter sphaeroides complex. Biochim Biophys Acta. 2005 Nov 15;1710(1):34-46. doi: 10.1016/j.bbabio.2005.08.005. Epub 2005 Sep 8. PMID: 16181607.

15: Staśkowiak E, Dudkowiak A. Photostability and the yield of triplet state generation of bacteriochlorophyll c and bacteriopheophytin c in solution. Spectrochim Acta A Mol Biomol Spectrosc. 2005 Jul;61(9):2033-9. doi: 10.1016/j.saa.2004.08.004. PMID: 15911389.

16: Shkuropatov AY, Neerken S, Permentier HP, de Wijn R, Schmidt KA, Shuvalov VA, Aartsma TJ, Gast P, Hoff AJ. The effect of exchange of bacteriopheophytin a with plant pheophytin a on charge separation in Y(M210)W mutant reaction centers of Rhodobacter sphaeroides at low temperature. Biochim Biophys Acta. 2003 Mar 6;1557(1-3):1-12. doi: 10.1016/s0005-2728(02)00373-0. PMID: 12615343.

17: Addlesee HA, Hunter CN. Rhodospirillum rubrum possesses a variant of the bchP gene, encoding geranylgeranyl-bacteriopheophytin reductase. J Bacteriol. 2002 Mar;184(6):1578-86. doi: 10.1128/JB.184.6.1578-1586.2002. PMID: 11872709; PMCID: PMC134874.

18: Müh F, Bibikova M, Schlodder E, Oesterhelt D, Lubitz W. Conformational relaxation following reduction of the photoactive bacteriopheophytin in reaction centers from Balstochloris viridis. Influence of mutations at position M208. Biochim Biophys Acta. 2000 Jul 20;1459(1):191-201. PMID: 10924911.

19: Müh F, Bibikova M, Schlodder E, Oesterhelt D, Lubitz W. Conformational relaxation following reduction of the photoactive bacteriopheophytin in reaction centers from Blastochloris viridis. Influence of mutations at position M208. Biochim Biophys Acta. 2000 Jul 20;1459(1):191-201. PMID: 11004434.

20: Lapouge K, Näveke A, Robert B, Scheer H, Sturgis JN. Exchanging cofactors in the core antennae from purple bacteria: structure and properties of Zn- bacteriopheophytin-containing LH1. Biochemistry. 2000 Feb 8;39(5):1091-9. doi: 10.1021/bi991423k. PMID: 10653655.