Cord factor

Cord factor
Identifiers
CAS Number	61512-20-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	397861;
PubChem CID	451713;
	InChI InChI=1S/C130H250O15/c1-5-9-13-17-21-25-29-33-37-41-43-45-47-49-51-53-57-61-65-71-81-89-97-105-117(131)116(104-96-88-80-74-73-78-86-94-102-114-108-112(114)100-92-84-76-68-63-59-55-40-36-32-28-24-20-16-12-8-4)128(140)142-110-120-122(134)124(136)126(138)130(144-120)145-129-125(137)123(135)121(133)119(143-129)109-141-127(139)115(103-95-87-79-70-64-60-56-52-50-48-46-44-42-38-34-30-26-22-18-14-10-6-2)118(132)106-98-90-82-72-66-69-77-85-93-101-113-107-111(113)99-91-83-75-67-62-58-54-39-35-31-27-23-19-15-11-7-3/h111-126,129-138H,5-110H2,1-4H3 Key: DJUMKUNMJWRLAX-UHFFFAOYSA-N;
	SMILES CCCCCCCCCCCCCCCCCCCCCCCCCC(C(CCCCCCCCCCC1CC1CCCCCCCCCCCCCCCCCC)C(=O)OCC2C(C(C(C(O2)OC3C(C(C(C(O3)COC(=O)C(CCCCCCCCCCCCCCCCCCCCCCCC)C(CCCCCCCCCCCC4CC4CCCCCCCCCCCCCCCCCC)O)O)O)O)O)O)O)O;
Properties
Chemical formula	C130H250O15
Molar mass	2053.415 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Cord factor, or trehalose dimycolate (TDM), is a glycolipid molecule found in the cell wall of Mycobacterium tuberculosis and similar species. It is the primary lipid found on the exterior of M. tuberculosis cells.^[1] Cord factor influences the arrangement of M. tuberculosis cells into long and slender formations, giving its name.^[2] Cord factor is virulent towards mammalian cells and critical for survival of M. tuberculosis in hosts, but not outside of hosts.^[3]^[4] Cord factor has been observed to influence immune responses, induce the formation of granulomas, and inhibit tumor growth.^[5] The antimycobacterial drug SQ109 is thought to inhibit TDM production levels and in this way disrupts its cell wall assembly.^[6]

^ Hunter, RL; Olsen, MR; Jagannath, C; Actor, JK (Autumn 2006). "Multiple roles of cord factor in the pathogenesis of primary, secondary, and cavitary tuberculosis, including a revised description of the pathology of secondary disease". Annals of Clinical and Laboratory Science. 36 (4): 371–86. PMID 17127724.
^ Saita, N.; Fujiwara, N.; Yano, I.; Soejima, K.; Kobayashi, K. (1 October 2000). "Trehalose 6,6'-Dimycolate (Cord Factor) of Mycobacterium tuberculosis Induces Corneal Angiogenesis in Rats". Infection and Immunity. 68 (10): 5991–5997. doi:10.1128/IAI.68.10.5991-5997.2000. PMC 101563. PMID 10992511.
^ Rajni; Rao, N; Meena, LS (2011). "Biosynthesis and Virulent Behavior of Lipids Produced by Mycobacterium tuberculosis: LAM and Cord Factor: An Overview". Biotechnology Research International. 2011: 274693. doi:10.4061/2011/274693. PMC 3039431. PMID 21350659.
^ Silva, CL; Ekizlerian, SM; Fazioli, RA (February 1985). "Role of cord factor in the modulation of infection caused by mycobacteria". The American Journal of Pathology. 118 (2): 238–47. PMC 1887869. PMID 3881973.
^ Spargo, BJ; Crowe, LM; Ioneda, T; Beaman, BL; Crowe, JH (Feb 1, 1991). "Cord factor (alpha,alpha-trehalose 6,6'-dimycolate) inhibits fusion between phospholipid vesicles". Proceedings of the National Academy of Sciences of the United States of America. 88 (3): 737–40. Bibcode:1991PNAS...88..737S. doi:10.1073/pnas.88.3.737. PMC 50888. PMID 1992465.
^ TAHLAN, K., R. WILSON, D. B. KASTRINSKY, K. ARORA, V. NAIR, E. FISCHER, S. W. BARNES, J. R. WALKER, D. ALLAND, C. E. BARRY a H. I. BOSHOFF. SQ109 Targets MmpL3, a Membrane Transporter of Trehalose Monomycolate Involved in Mycolic Acid Donation to the Cell Wall Core of Mycobacterium tuberculosis. Antimicrobial Agents and Chemotherapy. 2012-03-16, vol. 56, issue 4, s. 1797-1809. DOI: 10.1128/AAC.05708-11. http://aac.asm.org/cgi/doi/10.1128/AAC.05708-11

[multipleroles-1] Hunter, RL; Olsen, MR; Jagannath, C; Actor, JK (Autumn 2006). "Multiple roles of cord factor in the pathogenesis of primary, secondary, and cavitary tuberculosis, including a revised description of the pathology of secondary disease". Annals of Clinical and Laboratory Science. 36 (4): 371–86. PMID 17127724.

[2] Saita, N.; Fujiwara, N.; Yano, I.; Soejima, K.; Kobayashi, K. (1 October 2000). "Trehalose 6,6'-Dimycolate (Cord Factor) of Mycobacterium tuberculosis Induces Corneal Angiogenesis in Rats". Infection and Immunity. 68 (10): 5991–5997. doi:10.1128/IAI.68.10.5991-5997.2000. PMC 101563. PMID 10992511.

[biosynth-3] Rajni; Rao, N; Meena, LS (2011). "Biosynthesis and Virulent Behavior of Lipids Produced by Mycobacterium tuberculosis: LAM and Cord Factor: An Overview". Biotechnology Research International. 2011: 274693. doi:10.4061/2011/274693. PMC 3039431. PMID 21350659.

[4] Silva, CL; Ekizlerian, SM; Fazioli, RA (February 1985). "Role of cord factor in the modulation of infection caused by mycobacteria". The American Journal of Pathology. 118 (2): 238–47. PMC 1887869. PMID 3881973.

[fusion-5] Spargo, BJ; Crowe, LM; Ioneda, T; Beaman, BL; Crowe, JH (Feb 1, 1991). "Cord factor (alpha,alpha-trehalose 6,6'-dimycolate) inhibits fusion between phospholipid vesicles". Proceedings of the National Academy of Sciences of the United States of America. 88 (3): 737–40. Bibcode:1991PNAS...88..737S. doi:10.1073/pnas.88.3.737. PMC 50888. PMID 1992465.

[6] TAHLAN, K., R. WILSON, D. B. KASTRINSKY, K. ARORA, V. NAIR, E. FISCHER, S. W. BARNES, J. R. WALKER, D. ALLAND, C. E. BARRY a H. I. BOSHOFF. SQ109 Targets MmpL3, a Membrane Transporter of Trehalose Monomycolate Involved in Mycolic Acid Donation to the Cell Wall Core of Mycobacterium tuberculosis. Antimicrobial Agents and Chemotherapy. 2012-03-16, vol. 56, issue 4, s. 1797-1809. DOI: 10.1128/AAC.05708-11. http://aac.asm.org/cgi/doi/10.1128/AAC.05708-11

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Identifiers

CAS Number	61512-20-7^N
3D model (JSmol)	Interactive image
ChemSpider	397861
PubChem CID	451713
InChI InChI=1S/C130H250O15/c1-5-9-13-17-21-25-29-33-37-41-43-45-47-49-51-53-57-61-65-71-81-89-97-105-117(131)116(104-96-88-80-74-73-78-86-94-102-114-108-112(114)100-92-84-76-68-63-59-55-40-36-32-28-24-20-16-12-8-4)128(140)142-110-120-122(134)124(136)126(138)130(144-120)145-129-125(137)123(135)121(133)119(143-129)109-141-127(139)115(103-95-87-79-70-64-60-56-52-50-48-46-44-42-38-34-30-26-22-18-14-10-6-2)118(132)106-98-90-82-72-66-69-77-85-93-101-113-107-111(113)99-91-83-75-67-62-58-54-39-35-31-27-23-19-15-11-7-3/h111-126,129-138H,5-110H2,1-4H3 Key: DJUMKUNMJWRLAX-UHFFFAOYSA-N
SMILES CCCCCCCCCCCCCCCCCCCCCCCCCC(C(CCCCCCCCCCC1CC1CCCCCCCCCCCCCCCCCC)C(=O)OCC2C(C(C(C(O2)OC3C(C(C(C(O3)COC(=O)C(CCCCCCCCCCCCCCCCCCCCCCCC)C(CCCCCCCCCCCC4CC4CCCCCCCCCCCCCCCCCC)O)O)O)O)O)O)O)O
Properties
Chemical formula	C₁₃₀H₂₅₀O₁₅
Molar mass	2053.415 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

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Cord factor

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