Caldarchaeol

Caldarchaeol

IUPAC name [(2R,7R,11R,15S,19S, 22S,26S,30R,34R,38R,43R,47R, 51S,55S,58S,62S,66R,70R)- 38-(Hydroxymethyl)- 7,11,15,19,22,26,30,34,43,47,51,55,58,62,66,70-hexadecamethyl- 1,4,37,40-tetraoxacyclodoheptacont-2-yl]methanol
Other names Dibiphytanyldiglycerol tetraether
Identifiers
CAS number	99529-31-4
PubChem	5771745
ChemSpider	4696841^Y
Jmol-3D images	Image 1 Image 2
SMILES CC1CCCC(CCCC(CCOCC(OCCC(CCCC(CCCC(CCCC(CCC (CCCC(CCCC(CCCC(CCOCC(OCCC(CCCC(CCCC(CCCC(CCC (CCC1)C)C)C)C)C)CO)C)C)C)C)C)C)C)C)CO)C)C CC1CCCC(CCCC(CCOCC(OCCC(CCCC(CCCC(CCCC(CCC(CCCC(CCCC(CCCC(CCOCC(OCCC(CCCC(CCCC(CCCC(CCC(CCC1)C)C)C)C)C)CO)C)C)C)C)C)C)C)C)CO)C)C
InChI InChI=1S/C86H172O6/c1-69-29-17-33-73(5)41-25-49-81(13)57-61-89-67-85(65-87)91-63-59-83(15)52-28-44-76(8)36-20-32-72(4)40-24-48-80(12)56-54-78(10)46-22-38-70(2)30-18-34-74(6)42-26-50-82(14)58-62-90-68-86(66-88)92-64-60-84(16)51-27-43-75(7)35-19-31-71(3)39-23-47-79(11)55-53-77(9)45-21-37-69/h69-88H,17-68H2,1-16H3/t69-,70-,71-,72-,73+,74+,75+,76+,77-,78-,79-,80-,81+,82+,83+,84+,85+,86+/m0/s1^Y Key: VMHUDYKDOMRJOK-QUYWEVSVSA-N^Y InChI=1/C86H172O6/c1-69-29-17-33-73(5)41-25-49-81(13)57-61-89-67-85(65-87)91-63-59-83(15)52-28-44-76(8)36-20-32-72(4)40-24-48-80(12)56-54-78(10)46-22-38-70(2)30-18-34-74(6)42-26-50-82(14)58-62-90-68-86(66-88)92-64-60-84(16)51-27-43-75(7)35-19-31-71(3)39-23-47-79(11)55-53-77(9)45-21-37-69/h69-88H,17-68H2,1-16H3/t69-,70-,71-,72-,73+,74+,75+,76+,77-,78-,79-,80-,81+,82+,83+,84+,85+,86+/m0/s1 Key: VMHUDYKDOMRJOK-QUYWEVSVBU
Properties
Molecular formula	C₈₆H₁₇₂O₆
Molar mass	1302.28 g/mol
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Caldarchaeol is a membrane-spanning lipid found in hyperthermophilic archaea. Membranes made up of caldarchaeol are more stable since the hydrophobic chains are linked together, allowing the microorganisms to withstand high temperatures. It is also known as dibiphytanyldiglycerol tetraether. Two glycerol units are linked together by two strains which consist of two phytanes linked together to form a linear chain of 32 carbon atoms (40 carbons including methyl sidechains).

The configuration of the macrocyclic tetraether has been determined by total synthesis of the C40-diol and comparison with a sample of obtained by degradation of natural tetraether.^[1] A synthesis of tertaether has also been carried out.^[2]

Notes

^ C. H. Heathcock, B. L. Finkelstein, E. T. Jarvi, P. A. Radel, C. R. Hadley (1988). "Acyclic stereoselection. Part 42. 1,4- and 1,5-Stereoselection by sequential aldol addition to a .alpha.,.beta.-unsaturated aldehydes followed by Claisen rearrangement. Application to total synthesis of the vitamin E side chain and the archaebacterial C40 diol". J. Org. Chem. 53 (9): 1922–1942. doi:10.1021/jo00244a017.
^ T. Eguchi, K. Ibaragi, K. Kakinuma (1998). "Total Synthesis of Archaeal 72-Membered Macrocyclic Tetraether Lipids". J. Org. Chem. 63 (8): 2689–2698. doi:10.1021/jo972328p. PMID 11672138.

Additional references

Focus of research, University of Occupational and Environmental Health, Kitakyushu, Japan
Langworthy TA, Biochim Biophys Acta 1977, 487, 37
Monolayer properties of archaeol and caldarchaeol polar lipids of a methanogenic archaebacterium, Methanospirillum hungatei, at the air/water interface. Tomoaia-Cotisel M, Chifu E, Zsako J, Mocanu A, Quinn PJ, Kates M. Chem Phys Lipids. 1992 Nov;63(1-2):131-8
Ether polar lipids of methanogenic bacteria: structures, comparative aspects, and biosyntheses. Koga Y, Nishihara M, Morii H, Akagawa-Matsushita M. Microbiol Rev. 1993 Mar;57(1):164-82.