Synthesis and NMR identification of isobutyl analogs of phospholipids designed for the modeling of biomembrane fragments

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Synthesis and NMR identification of isobutyl analogs of phospholipids designed for the modeling of biomembrane fragments. / Karasev, V. A.; Korovnikova, N. A.; Gindin, V. A.; Stefanov, V. E.

In: Colloids and Surfaces A: Physicochemical and Engineering Aspects, Vol. 115, 30.08.1996, p. 83-87.

Research output: Contribution to journal › Conference article › peer-review

Author

Karasev, V. A. ; Korovnikova, N. A. ; Gindin, V. A. ; Stefanov, V. E. / Synthesis and NMR identification of isobutyl analogs of phospholipids designed for the modeling of biomembrane fragments. In: Colloids and Surfaces A: Physicochemical and Engineering Aspects. 1996 ; Vol. 115. pp. 83-87.

BibTeX

@article{e6c188f548794119ac938223efd5a85a,

title = "Synthesis and NMR identification of isobutyl analogs of phospholipids designed for the modeling of biomembrane fragments",

abstract = "Three isobutyl analogs of phospholipids - isobutyl phosphoric acid (IPA), analog of phosphatidic acid; isobutyl phosphoethanolamine (IPE), analog of phosphatidylethanolamine; and isobutyl phosphocholine (IPCh), analog of phosphatidylcholine - were synthesized for use in mixed crystals as initial material for modeling biomembrane fragments. Isobutyl oxophosphodichloride served as a common precursor yielding IPA when hydrolyzed. Cyclic compounds of the former with ethanolamine and ethylene glycol were used to synthesize IPE and IPCh. The structure of the obtained compounds was identified by means of NMR. For all three compounds the following signals were registered (ppm): 0.9, d, 6H, (CH3)2CH-; 1.9, m, 1H, (CH3)2CH-; 3.7, t, 2H, -P-O-CH2-CH(CH3)2; which can be attributed to the isobutyl radical. In addition, the following signals were registered for IPE: 3.3, t, 2H, -P-O-CH2-CH2-NH2; 4.1, m, 2H, -P-O-CH2-CH2-NH2; and for IPCh: 3.2, s, 9H, -CH2-CH2-N+(CH3)3; 4.2, m, 2H, -P-O-CH2-CH2-N+(CH3)3. X-ray analysis of the crystals is in progress as part of model studies of the biomembrane organization.",

keywords = "biomembrane fragment modelling, isobutyl analogs, NMR identification, phospholipids, synthesis",

author = "Karasev, {V. A.} and Korovnikova, {N. A.} and Gindin, {V. A.} and Stefanov, {V. E.}",

year = "1996",

month = aug,

day = "30",

doi = "10.1016/0927-7757(96)03609-6",

language = "English",

volume = "115",

pages = "83--87",

journal = "Colloids and Surfaces A: Physicochemical and Engineering Aspects",

issn = "0927-7757",

publisher = "Elsevier",

note = "Proceedings of the 1996 7th International Symposium on Magnetic Resonanace in Colloid and Interface Science ; Conference date: 11-09-1996 Through 15-09-1996",

}

RIS

TY - JOUR

T1 - Synthesis and NMR identification of isobutyl analogs of phospholipids designed for the modeling of biomembrane fragments

AU - Karasev, V. A.

AU - Korovnikova, N. A.

AU - Gindin, V. A.

AU - Stefanov, V. E.

PY - 1996/8/30

Y1 - 1996/8/30

N2 - Three isobutyl analogs of phospholipids - isobutyl phosphoric acid (IPA), analog of phosphatidic acid; isobutyl phosphoethanolamine (IPE), analog of phosphatidylethanolamine; and isobutyl phosphocholine (IPCh), analog of phosphatidylcholine - were synthesized for use in mixed crystals as initial material for modeling biomembrane fragments. Isobutyl oxophosphodichloride served as a common precursor yielding IPA when hydrolyzed. Cyclic compounds of the former with ethanolamine and ethylene glycol were used to synthesize IPE and IPCh. The structure of the obtained compounds was identified by means of NMR. For all three compounds the following signals were registered (ppm): 0.9, d, 6H, (CH3)2CH-; 1.9, m, 1H, (CH3)2CH-; 3.7, t, 2H, -P-O-CH2-CH(CH3)2; which can be attributed to the isobutyl radical. In addition, the following signals were registered for IPE: 3.3, t, 2H, -P-O-CH2-CH2-NH2; 4.1, m, 2H, -P-O-CH2-CH2-NH2; and for IPCh: 3.2, s, 9H, -CH2-CH2-N+(CH3)3; 4.2, m, 2H, -P-O-CH2-CH2-N+(CH3)3. X-ray analysis of the crystals is in progress as part of model studies of the biomembrane organization.

AB - Three isobutyl analogs of phospholipids - isobutyl phosphoric acid (IPA), analog of phosphatidic acid; isobutyl phosphoethanolamine (IPE), analog of phosphatidylethanolamine; and isobutyl phosphocholine (IPCh), analog of phosphatidylcholine - were synthesized for use in mixed crystals as initial material for modeling biomembrane fragments. Isobutyl oxophosphodichloride served as a common precursor yielding IPA when hydrolyzed. Cyclic compounds of the former with ethanolamine and ethylene glycol were used to synthesize IPE and IPCh. The structure of the obtained compounds was identified by means of NMR. For all three compounds the following signals were registered (ppm): 0.9, d, 6H, (CH3)2CH-; 1.9, m, 1H, (CH3)2CH-; 3.7, t, 2H, -P-O-CH2-CH(CH3)2; which can be attributed to the isobutyl radical. In addition, the following signals were registered for IPE: 3.3, t, 2H, -P-O-CH2-CH2-NH2; 4.1, m, 2H, -P-O-CH2-CH2-NH2; and for IPCh: 3.2, s, 9H, -CH2-CH2-N+(CH3)3; 4.2, m, 2H, -P-O-CH2-CH2-N+(CH3)3. X-ray analysis of the crystals is in progress as part of model studies of the biomembrane organization.

KW - biomembrane fragment modelling

KW - isobutyl analogs

KW - NMR identification

KW - phospholipids

KW - synthesis

UR - http://www.scopus.com/inward/record.url?scp=0342502062&partnerID=8YFLogxK

U2 - 10.1016/0927-7757(96)03609-6

DO - 10.1016/0927-7757(96)03609-6

M3 - Conference article

AN - SCOPUS:0342502062

VL - 115

SP - 83

EP - 87

JO - Colloids and Surfaces A: Physicochemical and Engineering Aspects

JF - Colloids and Surfaces A: Physicochemical and Engineering Aspects

SN - 0927-7757

T2 - Proceedings of the 1996 7th International Symposium on Magnetic Resonanace in Colloid and Interface Science

Y2 - 11 September 1996 through 15 September 1996

ER -

ID: 89842972