Chemical Synthesis and Self-Assembly of a Ladderane Phospholipid

Jaron A M Mercer; Carolyn M. Cohen; Steven R. Shuken; Anna M. Wagner; Myles W. Smith; Frank R. Moss; Matthew D. Smith; Riku Vahala; Alejandro Gonzalez-Martinez; Steven G. Boxer; Noah Z. Burns

doi:10.1021/jacs.6b10706

Chemical Synthesis and Self-Assembly of a Ladderane Phospholipid

Jaron A M Mercer, Carolyn M. Cohen, Steven R. Shuken, Anna M. Wagner, Myles W. Smith, Frank R. Moss, Matthew D. Smith, Riku Vahala, Alejandro Gonzalez-Martinez^*, Steven G. Boxer, Noah Z. Burns

^*Tämän työn vastaava kirjoittaja

Stanford University

Tutkimustuotos: Lehtiartikkeli › Article › Scientific › vertaisarvioitu

81 Sitaatiot (Scopus)

Abstrakti

Ladderane lipids produced by anammox bacteria constitute some of the most structurally fascinating yet poorly studied molecules among biological membrane lipids. Slow growth of the producing organism and the inherent difficulty of purifying complex lipid mixtures have prohibited isolation of useful amounts of natural ladderane lipids. We have devised a highly selective total synthesis of ladderane lipid tails and a full phosphatidylcholine to enable biophysical studies on chemically homogeneous samples of these molecules. Additionally, we report the first proof of absolute configuration of a natural ladderane.

Alkuperäiskieli	Englanti
Sivut	15845-15848
Sivumäärä	4
Julkaisu	Journal of the American Chemical Society
Vuosikerta	138
Numero	49
DOI - pysyväislinkit	https://doi.org/10.1021/jacs.6b10706
Tila	Julkaistu - 14 jouluk. 2016
OKM-julkaisutyyppi	A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä

Pääsy asiakirjaan

10.1021/jacs.6b10706

http://europepmc.org/backend/ptpmcrender.fcgi?accid=PMC5279923&blobtype=pdf

Muut tiedostot ja linkit

Link to publication in Scopus

CCDC 1527455: Experimental Crystal Structure Determination
Mercer, J. A. M. (Creator), Cohen, C. M. (Creator), Shuken, S. R. (Creator), Wagner, A. M. (Contributor), Smith, M. W. (Creator), Moss, F. R. (Creator), Smith, M. D. (Creator), Vahala, R. (Creator), Gonzalez Martinez, A. (Creator), Boxer, S. G. (Creator) & Burns, N. Z. (Creator), Cambridge Crystallographic Data Centre , 13 tammik. 2017
DOI - pysyväislinkki: 10.5517/ccdc.csd.cc1n8fr3, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1n8fr3&sid=DataCite
Tietoaineisto: Dataset
CCDC 1527452: Experimental Crystal Structure Determination
Mercer, J. A. M. (Creator), Cohen, C. M. (Creator), Shuken, S. R. (Creator), Wagner, A. M. (Creator), Smith, M. W. (Creator), Moss, F. R. (Creator), Smith, M. D. (Creator), Vahala, R. (Creator), Gonzalez Martinez, A. (Creator), Boxer, S. G. (Creator) & Burns, N. Z. (Creator), Cambridge Crystallographic Data Centre , 13 tammik. 2017
DOI - pysyväislinkki: 10.5517/ccdc.csd.cc1n8fn0, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1n8fn0&sid=DataCite
Tietoaineisto: Dataset
CCDC 1527454: Experimental Crystal Structure Determination
Boxer, S. G. (Contributor), Burns, N. Z. (Contributor), Cohen, C. M. (Contributor), Mercer, J. A. M. (Contributor), Shuken, S. R. (Contributor), Smith, M. W. (Contributor), Smith, M. W. (Contributor), Vahala, R. (Creator) & Wagner, A. M. (Contributor), Cambridge Crystallographic Data Centre , 1 tammik. 2017
DOI - pysyväislinkki: 10.5517/ccdc.csd.cc1n8fq2, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1n8fq2&sid=DataCite
Tietoaineisto: Dataset

Siteeraa tätä

@article{dcae084a6268466fa4f58ff4c0fcb3e6,

title = "Chemical Synthesis and Self-Assembly of a Ladderane Phospholipid",

abstract = "Ladderane lipids produced by anammox bacteria constitute some of the most structurally fascinating yet poorly studied molecules among biological membrane lipids. Slow growth of the producing organism and the inherent difficulty of purifying complex lipid mixtures have prohibited isolation of useful amounts of natural ladderane lipids. We have devised a highly selective total synthesis of ladderane lipid tails and a full phosphatidylcholine to enable biophysical studies on chemically homogeneous samples of these molecules. Additionally, we report the first proof of absolute configuration of a natural ladderane.",

author = "Mercer, {Jaron A M} and Cohen, {Carolyn M.} and Shuken, {Steven R.} and Wagner, {Anna M.} and Smith, {Myles W.} and Moss, {Frank R.} and Smith, {Matthew D.} and Riku Vahala and Alejandro Gonzalez-Martinez and Boxer, {Steven G.} and Burns, {Noah Z.}",

year = "2016",

month = dec,

day = "14",

doi = "10.1021/jacs.6b10706",

language = "English",

volume = "138",

pages = "15845--15848",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "49",

}

TY - JOUR

T1 - Chemical Synthesis and Self-Assembly of a Ladderane Phospholipid

AU - Mercer, Jaron A M

AU - Cohen, Carolyn M.

AU - Shuken, Steven R.

AU - Wagner, Anna M.

AU - Smith, Myles W.

AU - Moss, Frank R.

AU - Smith, Matthew D.

AU - Vahala, Riku

AU - Gonzalez-Martinez, Alejandro

AU - Boxer, Steven G.

AU - Burns, Noah Z.

PY - 2016/12/14

Y1 - 2016/12/14

N2 - Ladderane lipids produced by anammox bacteria constitute some of the most structurally fascinating yet poorly studied molecules among biological membrane lipids. Slow growth of the producing organism and the inherent difficulty of purifying complex lipid mixtures have prohibited isolation of useful amounts of natural ladderane lipids. We have devised a highly selective total synthesis of ladderane lipid tails and a full phosphatidylcholine to enable biophysical studies on chemically homogeneous samples of these molecules. Additionally, we report the first proof of absolute configuration of a natural ladderane.

AB - Ladderane lipids produced by anammox bacteria constitute some of the most structurally fascinating yet poorly studied molecules among biological membrane lipids. Slow growth of the producing organism and the inherent difficulty of purifying complex lipid mixtures have prohibited isolation of useful amounts of natural ladderane lipids. We have devised a highly selective total synthesis of ladderane lipid tails and a full phosphatidylcholine to enable biophysical studies on chemically homogeneous samples of these molecules. Additionally, we report the first proof of absolute configuration of a natural ladderane.

UR - http://www.scopus.com/inward/record.url?scp=85006247373&partnerID=8YFLogxK

U2 - 10.1021/jacs.6b10706

DO - 10.1021/jacs.6b10706

M3 - Article

AN - SCOPUS:85006247373

SN - 0002-7863

VL - 138

SP - 15845

EP - 15848

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 49

ER -

Chemical Synthesis and Self-Assembly of a Ladderane Phospholipid

Abstrakti

Pääsy asiakirjaan

Muut tiedostot ja linkit

Sormenjälki

Tietoaineistot

CCDC 1527455: Experimental Crystal Structure Determination

CCDC 1527452: Experimental Crystal Structure Determination

CCDC 1527454: Experimental Crystal Structure Determination

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