Synthesis of a macrocycle based on Linked Amino Acid Mimetics (LAAM)

David S. Maxwell; Duoli Sun; Zhenghong Peng; Diana V. Martin; Basvoju A. Bhanu Prasad; William G. Bornmann

doi:10.1016/j.tetlet.2013.08.041

Synthesis of a macrocycle based on Linked Amino Acid Mimetics (LAAM)

David S. Maxwell, Duoli Sun, Zhenghong Peng, Diana V. Martin, Basvoju A. Bhanu Prasad, William G. Bornmann

Research output: Contribution to journal › Article › peer-review

8 Scopus citations

Abstract

We report the synthesis of a macrocycle utilizing a novel framework of standard amino acids in combination with subunits that we have named as Linked Amino Acid Mimetics (LAAMs). Macrocycles based on the LAAM concept provide both a peptide targeting region and two independently variable functional regions. In the prototype structure, the commonly known Arg-Gly-Asp (RGD) sequence was used for the targeting region. The functional regions contain a phenyl group, and the linkage was formed via a Ring-Closing Metathesis (RCM) reaction.

Original language	English (US)
Pages (from-to)	5799-5801
Number of pages	3
Journal	Tetrahedron Letters
Volume	54
Issue number	43
DOIs	https://doi.org/10.1016/j.tetlet.2013.08.041
State	Published - Oct 23 2013
Externally published	Yes

Keywords

Amino Acid Mimetics
Auxiliary
LAAM
Macrocycle
RGD sequence
Ring-Closing Metathesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2013.08.041

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title = "Synthesis of a macrocycle based on Linked Amino Acid Mimetics (LAAM)",

abstract = "We report the synthesis of a macrocycle utilizing a novel framework of standard amino acids in combination with subunits that we have named as Linked Amino Acid Mimetics (LAAMs). Macrocycles based on the LAAM concept provide both a peptide targeting region and two independently variable functional regions. In the prototype structure, the commonly known Arg-Gly-Asp (RGD) sequence was used for the targeting region. The functional regions contain a phenyl group, and the linkage was formed via a Ring-Closing Metathesis (RCM) reaction.",

keywords = "Amino Acid Mimetics, Auxiliary, LAAM, Macrocycle, RGD sequence, Ring-Closing Metathesis",

author = "Maxwell, {David S.} and Duoli Sun and Zhenghong Peng and Martin, {Diana V.} and {Bhanu Prasad}, {Basvoju A.} and Bornmann, {William G.}",

note = "Funding Information: We acknowledge financial support from the John S. Dunn Gulf Coast Consortium for Chemical Genomics through the R.A. Welch Foundation Chemistry and Biology Collaborative Grant. The authors would also like to acknowledge the Cancer Center support grant CA016672 for the support of the translational chemistry core Facility and NMR facility at M.D. Anderson Cancer Center. ",

year = "2013",

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doi = "10.1016/j.tetlet.2013.08.041",

language = "English (US)",

volume = "54",

pages = "5799--5801",

journal = "Tetrahedron Letters",

issn = "0040-4039",

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TY - JOUR

T1 - Synthesis of a macrocycle based on Linked Amino Acid Mimetics (LAAM)

AU - Maxwell, David S.

AU - Sun, Duoli

AU - Peng, Zhenghong

AU - Martin, Diana V.

AU - Bhanu Prasad, Basvoju A.

AU - Bornmann, William G.

N1 - Funding Information: We acknowledge financial support from the John S. Dunn Gulf Coast Consortium for Chemical Genomics through the R.A. Welch Foundation Chemistry and Biology Collaborative Grant. The authors would also like to acknowledge the Cancer Center support grant CA016672 for the support of the translational chemistry core Facility and NMR facility at M.D. Anderson Cancer Center.

PY - 2013/10/23

Y1 - 2013/10/23

N2 - We report the synthesis of a macrocycle utilizing a novel framework of standard amino acids in combination with subunits that we have named as Linked Amino Acid Mimetics (LAAMs). Macrocycles based on the LAAM concept provide both a peptide targeting region and two independently variable functional regions. In the prototype structure, the commonly known Arg-Gly-Asp (RGD) sequence was used for the targeting region. The functional regions contain a phenyl group, and the linkage was formed via a Ring-Closing Metathesis (RCM) reaction.

AB - We report the synthesis of a macrocycle utilizing a novel framework of standard amino acids in combination with subunits that we have named as Linked Amino Acid Mimetics (LAAMs). Macrocycles based on the LAAM concept provide both a peptide targeting region and two independently variable functional regions. In the prototype structure, the commonly known Arg-Gly-Asp (RGD) sequence was used for the targeting region. The functional regions contain a phenyl group, and the linkage was formed via a Ring-Closing Metathesis (RCM) reaction.

KW - Amino Acid Mimetics

KW - Auxiliary

KW - LAAM

KW - Macrocycle

KW - RGD sequence

KW - Ring-Closing Metathesis

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DO - 10.1016/j.tetlet.2013.08.041

M3 - Article

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AN - SCOPUS:84884281706

SN - 0040-4039

VL - 54

SP - 5799

EP - 5801

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 43

ER -

Synthesis of a macrocycle based on Linked Amino Acid Mimetics (LAAM)

Abstract

Keywords

ASJC Scopus subject areas

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