Further studies toward the stereocontrolled synthesis of silicon-containing peptide mimics

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Further studies toward the stereocontrolled synthesis of silicon-containing peptide mimics. / Hernández, Dácil; Lindsay, Karl B; Nielsen, Lone; Mittag, Tina; Bjerglund, Klaus; Friis, Stig; Mose, Rasmus; Skrydstrup, Troels.

In: Journal of Organic Chemistry, Vol. 75, No. 10, 21.05.2010, p. 3283-93.

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaperJournal articleResearchpeer-review

Harvard

Hernández, D, Lindsay, KB, Nielsen, L, Mittag, T, Bjerglund, K, Friis, S, Mose, R & Skrydstrup, T 2010, 'Further studies toward the stereocontrolled synthesis of silicon-containing peptide mimics', Journal of Organic Chemistry, vol. 75, no. 10, pp. 3283-93. https://doi.org/10.1021/jo100301n

APA

Hernández, D., Lindsay, K. B., Nielsen, L., Mittag, T., Bjerglund, K., Friis, S., ... Skrydstrup, T. (2010). Further studies toward the stereocontrolled synthesis of silicon-containing peptide mimics. Journal of Organic Chemistry, 75(10), 3283-93. https://doi.org/10.1021/jo100301n

CBE

Hernández D, Lindsay KB, Nielsen L, Mittag T, Bjerglund K, Friis S, Mose R, Skrydstrup T. 2010. Further studies toward the stereocontrolled synthesis of silicon-containing peptide mimics. Journal of Organic Chemistry. 75(10):3283-93. https://doi.org/10.1021/jo100301n

MLA

Vancouver

Hernández D, Lindsay KB, Nielsen L, Mittag T, Bjerglund K, Friis S et al. Further studies toward the stereocontrolled synthesis of silicon-containing peptide mimics. Journal of Organic Chemistry. 2010 May 21;75(10):3283-93. https://doi.org/10.1021/jo100301n

Author

Hernández, Dácil ; Lindsay, Karl B ; Nielsen, Lone ; Mittag, Tina ; Bjerglund, Klaus ; Friis, Stig ; Mose, Rasmus ; Skrydstrup, Troels. / Further studies toward the stereocontrolled synthesis of silicon-containing peptide mimics. In: Journal of Organic Chemistry. 2010 ; Vol. 75, No. 10. pp. 3283-93.

Bibtex

@article{e763a9a2c3544f0590a81e5cf72950d6,
title = "Further studies toward the stereocontrolled synthesis of silicon-containing peptide mimics",
abstract = "Further studies are reported on the utilization of the versatile reaction between chiral sulfinimines and alkyldiphenylsilyl lithium reagents with the goal of preparing a wide range of silanediol-based protease inhibitors. In particular, focus has been placed to demonstrate how a number of genetically encoded amino acid side chains such as serine, threonine, tyrosine, lysine, proline, arginine, aspartate and asparagine might be incorporated into the overall approach. Efforts to apply this synthetic methodology for accessing biologically relevant silanediol dipeptide mimics are also described. This includes the synthesis of a potential inhibitor of the human neutrophil elastase, as well as a diphenylsilane mimic of a hexapeptide fragment of the human islet amyloid polypeptide.",
keywords = "Amino Acid Sequence, Humans, Leukocyte Elastase, Molecular Mimicry, Molecular Structure, Oligopeptides, Proteinase Inhibitory Proteins, Secretory, Silanes, Silicon, Stereoisomerism, Structure-Activity Relationship",
author = "D{\'a}cil Hern{\'a}ndez and Lindsay, {Karl B} and Lone Nielsen and Tina Mittag and Klaus Bjerglund and Stig Friis and Rasmus Mose and Troels Skrydstrup",
year = "2010",
month = "5",
day = "21",
doi = "10.1021/jo100301n",
language = "English",
volume = "75",
pages = "3283--93",
journal = "The Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "AMER CHEMICAL SOC",
number = "10",

}

RIS

TY - JOUR

T1 - Further studies toward the stereocontrolled synthesis of silicon-containing peptide mimics

AU - Hernández, Dácil

AU - Lindsay, Karl B

AU - Nielsen, Lone

AU - Mittag, Tina

AU - Bjerglund, Klaus

AU - Friis, Stig

AU - Mose, Rasmus

AU - Skrydstrup, Troels

PY - 2010/5/21

Y1 - 2010/5/21

N2 - Further studies are reported on the utilization of the versatile reaction between chiral sulfinimines and alkyldiphenylsilyl lithium reagents with the goal of preparing a wide range of silanediol-based protease inhibitors. In particular, focus has been placed to demonstrate how a number of genetically encoded amino acid side chains such as serine, threonine, tyrosine, lysine, proline, arginine, aspartate and asparagine might be incorporated into the overall approach. Efforts to apply this synthetic methodology for accessing biologically relevant silanediol dipeptide mimics are also described. This includes the synthesis of a potential inhibitor of the human neutrophil elastase, as well as a diphenylsilane mimic of a hexapeptide fragment of the human islet amyloid polypeptide.

AB - Further studies are reported on the utilization of the versatile reaction between chiral sulfinimines and alkyldiphenylsilyl lithium reagents with the goal of preparing a wide range of silanediol-based protease inhibitors. In particular, focus has been placed to demonstrate how a number of genetically encoded amino acid side chains such as serine, threonine, tyrosine, lysine, proline, arginine, aspartate and asparagine might be incorporated into the overall approach. Efforts to apply this synthetic methodology for accessing biologically relevant silanediol dipeptide mimics are also described. This includes the synthesis of a potential inhibitor of the human neutrophil elastase, as well as a diphenylsilane mimic of a hexapeptide fragment of the human islet amyloid polypeptide.

KW - Amino Acid Sequence

KW - Humans

KW - Leukocyte Elastase

KW - Molecular Mimicry

KW - Molecular Structure

KW - Oligopeptides

KW - Proteinase Inhibitory Proteins, Secretory

KW - Silanes

KW - Silicon

KW - Stereoisomerism

KW - Structure-Activity Relationship

U2 - 10.1021/jo100301n

DO - 10.1021/jo100301n

M3 - Journal article

C2 - 20423092

VL - 75

SP - 3283

EP - 3293

JO - The Journal of Organic Chemistry

JF - The Journal of Organic Chemistry

SN - 0022-3263

IS - 10

ER -