Bacteriochlorophyll a
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MedKoo CAT#: 330053

CAS#: 17499-98-8

Description: Bacteriochlorophyll a is a Bacteriochlorophyll from Rhodopseudomonas sphaeroides. Bacteriochlorophylls a, b, and g are bacteriochlorins, meaning their molecules have a bacteriochlorin macrocycle ring with two reduced pyrrole rings (B and D). Bacteriochlorophylls c, d, e, and f are chlorins, meaning their molecules have a chlorin macrocycle ring with one reduced pyrrole ring (D).


Price and Availability

Size Price Shipping out time Quantity
1mg USD 550 2 Weeks
5mg USD 1450 2 Weeks
1g USD 7950 3-4 months
Inquire bulk and customized quantity

Pricing updated 2020-12-02. Prices are subject to change without notice.

Bacteriochlorophyll a is in stock.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 330053
Name: Bacteriochlorophyll a
CAS#: 17499-98-8
Chemical Formula: C55H74MgN4O6
Exact Mass: 910.5459
Molecular Weight: 911.524
Elemental Analysis: C, 72.47; H, 8.18; Mg, 2.67; N, 6.15; O, 10.53


Synonym: Bacteriochlorophyll a; Bacteriochlorophyll; C11242; Bacteriochlorophyll from Rhodopseudomonas sphaeroides;

IUPAC/Chemical Name: magnesium;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]-23,25-diaza-7,24-diazanidahexacyclo[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: DSJXIQQMORJERS-AGGZHOMASA-M

InChi Code: InChI=1S/C55H75N4O6.Mg/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;/h25,27-32,34-35,39-40,51H,13-24,26H2,1-12H3,(H-,56,57,58,59,60,62);/q-1;+2/p-1/b33-25+;/t31-,32-,34-,35+,39-,40+,51-;/m1./s1

SMILES Code: CC[C@@H]1[C@H](C2=CC3=C(C(=C([N-]3)C=C4[C@H]([C@@H](C(=N4)C5=C6C(=C(C(=CC1=N2)[N-]6)C)C(=O)[C@@H]5C(=O)OC)CCC(=O)OC/C=C(\C)/CCC[C@H](C)CCC[C@H](C)CCCC(C)C)C)C)C(=O)C)C.[Mg+2]


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).

HS Tariff Code:
2934.99.9001


Additional Information

Bacteriochlorophylls (BChl) are photosynthetic pigments that occur in various phototrophic bacteria. They were discovered by C. B. van Niel in 1932. They are related to chlorophylls, which are the primary pigments in plants, algae, and cyanobacteria. Organisms that contain bacteriochlorophyll conduct photosynthesis to sustain their energy requirements, but do not produce oxygen as a byproduct. They use wavelengths of light not absorbed by plants or Cyanobacteria. Replacement of Mg2+ with protons gives bacteriophaeophytin (BPh), the phaeophytin form.
---from https://en.wikipedia.org/wiki/Bacteriochlorophyll.


References

1: Pankratov TA, Grouzdev DS, Patutina EO, Kolganova TV, Berestovskaya JJ, Ashikhmin AA. Lichenicoccus roseus gen. nov., sp. nov., the first bacteriochlorophyll a-containing, psychrophilic and acidophilic Acetobacteraceae bacteriobiont of lichen Cladonia species. Int J Syst Evol Microbiol. 2020 Aug;70(8):4591-4601. doi: 10.1099/ijsem.0.004318. Epub 2020 Jul 13. PMID: 32658637.

2: Charles P , Kalendra V , He Z , Khatami MH , Golbeck JH , van der Est A , Lakshmi KV , Bryant DA . Two-dimensional 67Zn HYSCORE spectroscopy reveals that a Zn-bacteriochlorophyll aP' dimer is the primary donor (P840) in the type-1 reaction centers of Chloracidobacterium thermophilum. Phys Chem Chem Phys. 2020 Mar 21;22(11):6457-6467. doi: 10.1039/c9cp06556c. Epub 2020 Mar 10. PMID: 32152610.

3: Hirose S, Tank M, Hara E, Tamaki H, Mori K, Takaichi S, Haruta S, Hanada S. Aquabacterium pictum sp. nov., the first aerobic bacteriochlorophyll a-containing fresh water bacterium in the genus Aquabacterium of the class Betaproteobacteria. Int J Syst Evol Microbiol. 2020 Jan;70(1):596-603. doi: 10.1099/ijsem.0.003798. PMID: 31622237.

4: Meneghin E, Pedron D, Collini E. Spectroscopy data for the time and frequency characterization of vibrational coherences in bacteriochlorophyll a. Data Brief. 2019 Mar 7;23:103707. doi: 10.1016/j.dib.2019.103707. PMID: 31372380; PMCID: PMC6660430.

5: Rätsep M, Linnanto JM, Freiberg A. Higher Order Vibronic Sidebands of Chlorophyll a and Bacteriochlorophyll a for Enhanced Excitation Energy Transfer and Light Harvesting. J Phys Chem B. 2019 Aug 22;123(33):7149-7156. doi: 10.1021/acs.jpcb.9b06843. Epub 2019 Aug 9. PMID: 31356081.

6: Anda A, Hansen T, De Vico L. Q y and Q x Absorption Bands for Bacteriochlorophyll a Molecules from LH2 and LH3. J Phys Chem A. 2019 Jun 27;123(25):5283-5292. doi: 10.1021/acs.jpca.9b02877. Epub 2019 Jun 18. PMID: 31242736.

7: Teramura M, Tsukatani Y, Harada J, Hirose M, Tamiaki H. Stereoselective C3-substituent modification and substrate channeling by oxidoreductase BchC in bacteriochlorophyll a biosynthesis. FEBS Lett. 2019 Apr;593(8):799-809. doi: 10.1002/1873-3468.13372. Epub 2019 Apr 4. PMID: 30908616.

8: Saga Y, Kawano K, Otsuka Y, Imanishi M, Kimura Y, Matsui S, Asakawa H. Selective oxidation of B800 bacteriochlorophyll a in photosynthetic light- harvesting protein LH2. Sci Rep. 2019 Mar 6;9(1):3636. doi: 10.1038/s41598-019-40082-y. PMID: 30842503; PMCID: PMC6403449.

9: Policht VR, Niedringhaus A, Ogilvie JP. Characterization of Vibrational Coherence in Monomeric Bacteriochlorophyll a by Two-Dimensional Electronic Spectroscopy. J Phys Chem Lett. 2018 Nov 15;9(22):6631-6637. doi: 10.1021/acs.jpclett.8b02691. Epub 2018 Nov 7. PMID: 30376340.

10: Irgen-Gioro S, Spencer AP, Hutson WO, Harel E. Coherences of Bacteriochlorophyll a Uncovered Using 3D-Electronic Spectroscopy. J Phys Chem Lett. 2018 Oct 18;9(20):6077-6081. doi: 10.1021/acs.jpclett.8b02217. Epub 2018 Oct 5. PMID: 30273488.

11: Saga Y, Hirota K, Matsui S, Asakawa H, Ishikita H, Saito K. Selective Removal of B800 Bacteriochlorophyll a from Light-Harvesting Complex 2 of the Purple Photosynthetic Bacterium Phaeospirillum molischianum. Biochemistry. 2018 May 29;57(21):3075-3083. doi: 10.1021/acs.biochem.8b00259. Epub 2018 May 17. PMID: 29771536.

12: Leiger K, Linnanto JM, Freiberg A. Vibronic Origin of the Qy Absorption Tail of Bacteriochlorophyll a Verified by Fluorescence Excitation Spectroscopy and Quantum Chemical Simulations. J Phys Chem Lett. 2017 Sep 7;8(17):4231-4235. doi: 10.1021/acs.jpclett.7b01704. Epub 2017 Aug 24. PMID: 28820595.

13: Saga Y, Hirota K, Asakawa H, Takao K, Fukuma T. Reversible Changes in the Structural Features of Photosynthetic Light-Harvesting Complex 2 by Removal and Reconstitution of B800 Bacteriochlorophyll a Pigments. Biochemistry. 2017 Jul 11;56(27):3484-3491. doi: 10.1021/acs.biochem.7b00267. Epub 2017 Jun 28. PMID: 28657308.

14: Zeng Y, Selyanin V, Lukeš M, Dean J, Kaftan D, Feng F, Koblížek M. Erratum: Characterization of the microaerophilic, bacteriochlorophyll a-containing bacterium Gemmatimonas phototrophica sp. nov., and emended descriptions of the genus Gemmatimonas and Gemmatimonas aurantiaca. Int J Syst Evol Microbiol. 2017 Feb;67(2):521-522. doi: 10.1099/ijsem.0.001859. Epub 2017 Feb 24. Erratum for: Int J Syst Evol Microbiol. 2015 Aug;65(8):2410-9. PMID: 28234578.

15: Zhang S, Lindsey JS. Construction of the Bacteriochlorin Macrocycle with Concomitant Nazarov Cyclization To Form the Annulated Isocyclic Ring: Analogues of Bacteriochlorophyll a. J Org Chem. 2017 Mar 3;82(5):2489-2504. doi: 10.1021/acs.joc.6b02878. Epub 2017 Feb 22. PMID: 28225270.

16: Kim CW, Rhee YM. Constructing an Interpolated Potential Energy Surface of a Large Molecule: A Case Study with Bacteriochlorophyll a Model in the Fenna- Matthews-Olson Complex. J Chem Theory Comput. 2016 Nov 8;12(11):5235-5246. doi: 10.1021/acs.jctc.6b00647. Epub 2016 Oct 28. PMID: 27760297.

17: Calvano CD, Ventura G, Trotta M, Bianco G, Cataldi TR, Palmisano F. Electron-Transfer Secondary Reaction Matrices for MALDI MS Analysis of Bacteriochlorophyll a in Rhodobacter sphaeroides and Its Zinc and Copper Analogue Pigments. J Am Soc Mass Spectrom. 2017 Jan;28(1):125-135. doi: 10.1007/s13361-016-1514-x. Epub 2016 Oct 11. PMID: 27730524.

18: Saga Y, Hirota K. Determination of the Molar Extinction Coefficients of the B800 and B850 Absorption Bands in Light-harvesting Complexes 2 Derived from Three Purple Photosynthetic Bacteria Rhodoblastus acidophilus, Rhodobacter sphaeroides, and Phaeospirillum molischianum by Extraction of Bacteriochlorophyll a. Anal Sci. 2016;32(7):801-4. doi: 10.2116/analsci.32.801. PMID: 27396664.

19: Lehours AC, Jeune AL, Aguer JP, Céréghino R, Corbara B, Kéraval B, Leroy C, Perrière F, Jeanthon C, Carrias JF. Unexpectedly high bacteriochlorophyll a concentrations in neotropical tank bromeliads. Environ Microbiol Rep. 2016 Oct;8(5):689-698. doi: 10.1111/1758-2229.12426. Epub 2016 Jul 12. PMID: 27264016.

20: Cardona T. Origin of Bacteriochlorophyll a and the Early Diversification of Photosynthesis. PLoS One. 2016 Mar 8;11(3):e0151250. doi: 10.1371/journal.pone.0151250. PMID: 26953697; PMCID: PMC4783071.