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Phosphatidylethanolamine

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Phosphatidylethanolamine

Biosynthesis of Phophatidylethanolamine in Bacteria

Phosphatidylethanolamines (sometimes abbreviated PE) are a class of phospholipids found in biological membranes.[1] They are synthesized by the addition of CDP-ethanolamine to diglycerides, releasing CMP. S-Adenosyl methionine can subsequently methylate the amine of phosphatidylethanolamines to yield phosphatidylcholines. It can mainly be found in the inner (cytoplasmic) leaflet of the lipid bilayer.[2]

Function

The major membrane lipids
PtdCho - Phosphatidylcholine;
PtdEtn - Phosphatidylethanolamine;
PtdIns -Phosphatidylinositol;
PtdSer - Phosphatidylserine.

In cells

Phosphatidylethanolamines are found in all living cells, composing 25% of all phospholipids. In human physiology, they are found particularly in nervous tissue such as the white matter of brain, nerves, neural tissue, and in spinal cord, where they make up 45% of all phospholipids.[3]

PEs play a role in membrane fusion and in disassembly of the contractile ring during cytokinesis in cell division.[4] Additionally, it is thought that PE regulates membrane curvature. PE acts as an important precursor, substrate, or donor in several biological pathways.[3]

As a polar head group, PE creates a more viscous lipid membrane compared to phosphatidylcholine (PC). For example, the melting temperature of di-oleoyl-PE is -16 °C while the melting temperature of di-oleoyl-PC is -20 °C. If the lipids had two palmitoyl chains, PE would melt at 63°C while PC would melt already at 41 °C.[5] Lower melting temperatures correspond, in a simplistic view, to more fluid membranes.

In humans

In humans, metabolism of PE is thought to be important in the heart. When blood flow to the heart is restricted, the asymmetrical distribution of PE between membrane leaflets is disrupted, and as a result the membrane is disrupted. Additionally, PE plays a role in the secretion of lipoproteins in the liver. This is because vesicles for secretion of VLDLs coming off of the Golgi have a significantly higher PE concentration when compared to other vesicles containing VLDLs.[6] PE has also shown to be able to propagate infectious prions without the assistance of any proteins or nucleic acids, which is a unique characteristic of it.[7] PE is also thought to play a role in blood clotting, as it works with phosphatidylserine to increase the rate of thrombin formation by promoting binding to Factor V and Factor X, two proteins which catalyze the formation of thrombin from prothrombin.[8]

In bacteria

Where phosphatidylcholine is the principal phospholipid in animals, PE is the principal one in bacteria. One of the primary roles for PE in bacterial membranes is to spread out the negative charge caused by anionic membrane phospholipids. In the bacterium E. coli, PE play a role in supporting lactose permease's active transport of lactose into the cell, and may play a role in other transport systems as well. PE plays a role in the assembly of lactose permease and other membrane proteins. It acts as a 'chaperone' to help the membrane proteins correctly fold their tertiary structures so that they can function properly. When PE is not present, the transport proteins have incorrect tertiary structures and do not function correctly.[9]

PE also enables bacterial multidrug transporters to function properly. PE allows the formation of intermediates that are needed for the transporters to properly open and close.[10]

Structure

As a lecithin, PE consists of a combination of glycerol esterified with two fatty acids and phosphoric acid. Whereas the phosphate group is combined with choline in phosphatidylcholine, it is combined with the ethanolamine in PE. The two fatty acids may be the same, or different, and are usually in the 1,2 positions (though they can be in the 1,3 positions).

Synthesis

The phosphatidylserine decarboxylation pathway and the CDP-ethanolamine pathways are used to synthesize PE. Phosphatidylserine decarboxylase (PSD) is the enzyme that is used to decarboxylate phosphatidylserine in the first pathway. The phosphatidylserine decarboxylation pathway is the main source of synthesis for PE in the membranes of the mitochondria. PE produced in the mitochondrial membrane is also transported throughout the cell to other membranes for use. In a process that mirrors phosphatidylcholine synthesis, PE is also made via the CDP-ethanolamine pathway, using ethanolamine as the substrate. Through several steps taking place is both the cytosol and endoplasmic reticulum, the synthesis pathway yields the end product of PE.[11] PE is also found abundantly in soya or egg lecithin and is produced commercially using chromatographic separation.

Regulation

Synthesis of PE through the phosphatidylserine decarboxylation pathway occurs rapidly in the inner mitochondrial membrane. However, phosphatidylserine is made in the endoplasmic reticulum. Because of this, the transport of phosphatidylserine from the endoplasmic reticulum to the mitrochondrial membrane and then to the inner mitochondrial membrane limits the rate of synthesis via this pathway. The mechanism for this transport is currently unknown, but may play a role in regulation of the rate of synthesis in this pathway.require('Module:No globals')

local p = {}

-- articles in which traditional Chinese preceeds simplified Chinese local t1st = { ["228 Incident"] = true, ["Chinese calendar"] = true, ["Lippo Centre, Hong Kong"] = true, ["Republic of China"] = true, ["Republic of China at the 1924 Summer Olympics"] = true, ["Taiwan"] = true, ["Taiwan (island)"] = true, ["Taiwan Province"] = true, ["Wei Boyang"] = true, }

-- the labels for each part local labels = { ["c"] = "Chinese", ["s"] = "simplified Chinese", ["t"] = "traditional Chinese", ["p"] = "pinyin", ["tp"] = "Tongyong Pinyin", ["w"] = "Wade–Giles", ["j"] = "Jyutping", ["cy"] = "Cantonese Yale", ["poj"] = "Pe̍h-ōe-jī", ["zhu"] = "Zhuyin Fuhao", ["l"] = "literally", }

-- article titles for wikilinks for each part local wlinks = { ["c"] = "Chinese language", ["s"] = "simplified Chinese characters", ["t"] = "traditional Chinese characters", ["p"] = "pinyin", ["tp"] = "Tongyong Pinyin", ["w"] = "Wade–Giles", ["j"] = "Jyutping", ["cy"] = "Yale romanization of Cantonese", ["poj"] = "Pe̍h-ōe-jī", ["zhu"] = "Bopomofo", }

-- for those parts which are to be treated as languages their ISO code local ISOlang = { ["c"] = "zh", ["t"] = "zh-Hant", ["s"] = "zh-Hans", ["p"] = "zh-Latn-pinyin", ["tp"] = "zh-Latn", ["w"] = "zh-Latn-wadegile", ["j"] = "yue-jyutping", ["cy"] = "yue", ["poj"] = "hak", ["zhu"] = "zh-Bopo", }

local italic = { ["p"] = true, ["tp"] = true, ["w"] = true, ["j"] = true, ["cy"] = true, ["poj"] = true, } -- Categories for different kinds of Chinese text local cats = { ["c"] = "", ["s"] = "", ["t"] = "", }

function p.Zh(frame) -- load arguments module to simplify handling of args local getArgs = require('Module:Arguments').getArgs local args = getArgs(frame) return p._Zh(args) end function p._Zh(args) local uselinks = not (args["links"] == "no") -- whether to add links local uselabels = not (args["labels"] == "no") -- whether to have labels local capfirst = args["scase"] ~= nil

        local t1 = false -- whether traditional Chinese characters go first
        local j1 = false -- whether Cantonese Romanisations go first
        local testChar
        if (args["first"]) then
                 for testChar in mw.ustring.gmatch(args["first"], "%a+") do
          if (testChar == "t") then
           t1 = true
           end
          if (testChar == "j") then
           j1 = true
           end
         end
        end
        if (t1 == false) then
         local title = mw.title.getCurrentTitle()
         t1 = t1st[title.text] == true
        end

-- based on setting/preference specify order local orderlist = {"c", "s", "t", "p", "tp", "w", "j", "cy", "poj", "zhu", "l"} if (t1) then orderlist[2] = "t" orderlist[3] = "s" end if (j1) then orderlist[4] = "j" orderlist[5] = "cy" orderlist[6] = "p" orderlist[7] = "tp" orderlist[8] = "w" end -- rename rules. Rules to change parameters and labels based on other parameters if args["hp"] then -- hp an alias for p ([hanyu] pinyin) args["p"] = args["hp"] end if args["tp"] then -- if also Tongyu pinyin use full name for Hanyu pinyin labels["p"] = "Hanyu Pinyin" end if (args["s"] and args["s"] == args["t"]) then -- Treat simplified + traditional as Chinese if they're the same args["c"] = args["s"] args["s"] = nil args["t"] = nil elseif (not (args["s"] and args["t"])) then -- use short label if only one of simplified and traditional labels["s"] = labels["c"] labels["t"] = labels["c"] end local body = "" -- the output string local params -- for creating HTML spans local label -- the label, i.e. the bit preceeding the supplied text local val -- the supplied text -- go through all possible fields in loop, adding them to the output for i, part in ipairs(orderlist) do if (args[part]) then -- build label label = "" if (uselabels) then label = labels[part] if (capfirst) then label = mw.language.getContentLanguage():ucfirst(

Presence in food, health issues

Phosphatidylethanolamines in food break down to form PE-linked Amadori products as a part of the Maillard reaction.[12] These products accelerate membrane lipid peroxidation, causing oxidative stress to cells that come in contact with them.[13] Oxidative stress is known to cause food deterioration and several diseases. Significant levels of Amadori-PE products have been found in a wide variety of foods such as chocolate, soybean milk, infant formula, and other processed foods. The levels of Amadori-PE products are higher in foods with high lipid and sugar concentrations that have high temperatures in processing.[12] Additional studies have found that Amadori-PE may play a role in vascular disease,[14] act as the mechanism by which diabetes can increase the incidence of cancer,[15] and potentially play a role in other diseases as well. Amadori-PE has a higher plasma concentration in diabetes patients than healthy people, indicating it may play a role in the development of the disease or be a product of the disease.[16]

See also

References


-- Module:Hatnote -- -- -- -- This module produces hatnote links and links to related articles. It -- -- implements the and meta-templates and includes -- -- helper functions for other Lua hatnote modules. --


local libraryUtil = require('libraryUtil') local checkType = libraryUtil.checkType local mArguments -- lazily initialise Module:Arguments local yesno -- lazily initialise Module:Yesno

local p = {}


-- Helper functions


local function getArgs(frame) -- Fetches the arguments from the parent frame. Whitespace is trimmed and -- blanks are removed. mArguments = require('Module:Arguments') return mArguments.getArgs(frame, {parentOnly = true}) end

local function removeInitialColon(s) -- Removes the initial colon from a string, if present. return s:match('^:?(.*)') end

function p.findNamespaceId(link, removeColon) -- Finds the namespace id (namespace number) of a link or a pagename. This -- function will not work if the link is enclosed in double brackets. Colons -- are trimmed from the start of the link by default. To skip colon -- trimming, set the removeColon parameter to true. checkType('findNamespaceId', 1, link, 'string') checkType('findNamespaceId', 2, removeColon, 'boolean', true) if removeColon ~= false then link = removeInitialColon(link) end local namespace = link:match('^(.-):') if namespace then local nsTable = mw.site.namespaces[namespace] if nsTable then return nsTable.id end end return 0 end

function p.formatPages(...) -- Formats a list of pages using formatLink and returns it as an array. Nil -- values are not allowed. local pages = {...} local ret = {} for i, page in ipairs(pages) do ret[i] = p._formatLink(page) end return ret end

function p.formatPageTables(...) -- Takes a list of page/display tables and returns it as a list of -- formatted links. Nil values are not allowed. local pages = {...} local links = {} for i, t in ipairs(pages) do checkType('formatPageTables', i, t, 'table') local link = t[1] local display = t[2] links[i] = p._formatLink(link, display) end return links end

function p.makeWikitextError(msg, helpLink, addTrackingCategory) -- Formats an error message to be returned to wikitext. If -- addTrackingCategory is not false after being returned from -- Module:Yesno, and if we are not on a talk page, a tracking category -- is added. checkType('makeWikitextError', 1, msg, 'string') checkType('makeWikitextError', 2, helpLink, 'string', true) yesno = require('Module:Yesno') local title = mw.title.getCurrentTitle() -- Make the help link text. local helpText if helpLink then helpText = ' (help)' else helpText = end -- Make the category text. local category if not title.isTalkPage and yesno(addTrackingCategory) ~= false then category = 'Hatnote templates with errors' category = string.format( '%s:%s', mw.site.namespaces[14].name, category ) else category = end return string.format( '%s', msg, helpText, category ) end


-- Format link -- -- Makes a wikilink from the given link and display values. Links are escaped -- with colons if necessary, and links to sections are detected and displayed -- with " § " as a separator rather than the standard MediaWiki "#". Used in -- the template.


function p.formatLink(frame) local args = getArgs(frame) local link = args[1] local display = args[2] if not link then return p.makeWikitextError( 'no link specified', 'Template:Format hatnote link#Errors', args.category ) end return p._formatLink(link, display) end

function p._formatLink(link, display) -- Find whether we need to use the colon trick or not. We need to use the -- colon trick for categories and files, as otherwise category links -- categorise the page and file links display the file. checkType('_formatLink', 1, link, 'string') checkType('_formatLink', 2, display, 'string', true) link = removeInitialColon(link) local namespace = p.findNamespaceId(link, false) local colon if namespace == 6 or namespace == 14 then colon = ':' else colon = end -- Find whether a faux display value has been added with the | magic -- word. if not display then local prePipe, postPipe = link:match('^(.-)|(.*)$') link = prePipe or link display = postPipe end -- Find the display value. if not display then local page, section = link:match('^(.-)#(.*)$') if page then display = page .. ' § ' .. section end end -- Assemble the link. if display then return string.format('%s', colon, link, display) else return string.format('%s%s', colon, link) end end


-- Hatnote -- -- Produces standard hatnote text. Implements the template.


function p.hatnote(frame) local args = getArgs(frame) local s = args[1] local options = {} if not s then return p.makeWikitextError( 'no text specified', 'Template:Hatnote#Errors', args.category ) end options.extraclasses = args.extraclasses options.selfref = args.selfref return p._hatnote(s, options) end

function p._hatnote(s, options) checkType('_hatnote', 1, s, 'string') checkType('_hatnote', 2, options, 'table', true) local classes = {'hatnote'} local extraclasses = options.extraclasses local selfref = options.selfref if type(extraclasses) == 'string' then classes[#classes + 1] = extraclasses end if selfref then classes[#classes + 1] = 'selfref' end return string.format( '
%s
', table.concat(classes, ' '), s )

end

return p-------------------------------------------------------------------------------- -- Module:Hatnote -- -- -- -- This module produces hatnote links and links to related articles. It -- -- implements the and meta-templates and includes -- -- helper functions for other Lua hatnote modules. --


local libraryUtil = require('libraryUtil') local checkType = libraryUtil.checkType local mArguments -- lazily initialise Module:Arguments local yesno -- lazily initialise Module:Yesno

local p = {}


-- Helper functions


local function getArgs(frame) -- Fetches the arguments from the parent frame. Whitespace is trimmed and -- blanks are removed. mArguments = require('Module:Arguments') return mArguments.getArgs(frame, {parentOnly = true}) end

local function removeInitialColon(s) -- Removes the initial colon from a string, if present. return s:match('^:?(.*)') end

function p.findNamespaceId(link, removeColon) -- Finds the namespace id (namespace number) of a link or a pagename. This -- function will not work if the link is enclosed in double brackets. Colons -- are trimmed from the start of the link by default. To skip colon -- trimming, set the removeColon parameter to true. checkType('findNamespaceId', 1, link, 'string') checkType('findNamespaceId', 2, removeColon, 'boolean', true) if removeColon ~= false then link = removeInitialColon(link) end local namespace = link:match('^(.-):') if namespace then local nsTable = mw.site.namespaces[namespace] if nsTable then return nsTable.id end end return 0 end

function p.formatPages(...) -- Formats a list of pages using formatLink and returns it as an array. Nil -- values are not allowed. local pages = {...} local ret = {} for i, page in ipairs(pages) do ret[i] = p._formatLink(page) end return ret end

function p.formatPageTables(...) -- Takes a list of page/display tables and returns it as a list of -- formatted links. Nil values are not allowed. local pages = {...} local links = {} for i, t in ipairs(pages) do checkType('formatPageTables', i, t, 'table') local link = t[1] local display = t[2] links[i] = p._formatLink(link, display) end return links end

function p.makeWikitextError(msg, helpLink, addTrackingCategory) -- Formats an error message to be returned to wikitext. If -- addTrackingCategory is not false after being returned from -- Module:Yesno, and if we are not on a talk page, a tracking category -- is added. checkType('makeWikitextError', 1, msg, 'string') checkType('makeWikitextError', 2, helpLink, 'string', true) yesno = require('Module:Yesno') local title = mw.title.getCurrentTitle() -- Make the help link text. local helpText if helpLink then helpText = ' (help)' else helpText = end -- Make the category text. local category if not title.isTalkPage and yesno(addTrackingCategory) ~= false then category = 'Hatnote templates with errors' category = string.format( '%s:%s', mw.site.namespaces[14].name, category ) else category = end return string.format( '%s', msg, helpText, category ) end


-- Format link -- -- Makes a wikilink from the given link and display values. Links are escaped -- with colons if necessary, and links to sections are detected and displayed -- with " § " as a separator rather than the standard MediaWiki "#". Used in -- the template.


function p.formatLink(frame) local args = getArgs(frame) local link = args[1] local display = args[2] if not link then return p.makeWikitextError( 'no link specified', 'Template:Format hatnote link#Errors', args.category ) end return p._formatLink(link, display) end

function p._formatLink(link, display) -- Find whether we need to use the colon trick or not. We need to use the -- colon trick for categories and files, as otherwise category links -- categorise the page and file links display the file. checkType('_formatLink', 1, link, 'string') checkType('_formatLink', 2, display, 'string', true) link = removeInitialColon(link) local namespace = p.findNamespaceId(link, false) local colon if namespace == 6 or namespace == 14 then colon = ':' else colon = end -- Find whether a faux display value has been added with the | magic -- word. if not display then local prePipe, postPipe = link:match('^(.-)|(.*)$') link = prePipe or link display = postPipe end -- Find the display value. if not display then local page, section = link:match('^(.-)#(.*)$') if page then display = page .. ' § ' .. section end end -- Assemble the link. if display then return string.format('%s', colon, link, display) else return string.format('%s%s', colon, link) end end


-- Hatnote -- -- Produces standard hatnote text. Implements the template.


function p.hatnote(frame) local args = getArgs(frame) local s = args[1] local options = {} if not s then return p.makeWikitextError( 'no text specified', 'Template:Hatnote#Errors', args.category ) end options.extraclasses = args.extraclasses options.selfref = args.selfref return p._hatnote(s, options) end

function p._hatnote(s, options) checkType('_hatnote', 1, s, 'string') checkType('_hatnote', 2, options, 'table', true) local classes = {'hatnote'} local extraclasses = options.extraclasses local selfref = options.selfref if type(extraclasses) == 'string' then classes[#classes + 1] = extraclasses end if selfref then classes[#classes + 1] = 'selfref' end return string.format( '
%s
', table.concat(classes, ' '), s )

end

return p
  1. ^
  2. ^
  3. ^ a b
  4. ^
  5. ^ See references in Wan et al. Biochemistry 47 2008
  6. ^
  7. ^
  8. ^
  9. ^
  10. ^
  11. ^
  12. ^ a b
  13. ^
  14. ^
  15. ^
  16. ^

External links

  • Phosphatidylethanolamines at the US National Library of Medicine Medical Subject Headings (MeSH)
  • Phosphatidylethanolamine at the The AOCS Lipid Library.
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