A simple and efficient synthesis of an Asp-Gly dipeptide mimetic

John M. Ndungu; Xuyuan Gu; Dustin E. Gross; Jinfa Ying; Victor J. Hruby

doi:10.1016/j.tetlet.2004.02.117

A simple and efficient synthesis of an Asp-Gly dipeptide mimetic

John M. Ndungu, Xuyuan Gu, Dustin E. Gross, Jinfa Ying, Victor J. Hruby

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

12 Scopus citations

Abstract

Alkylation of N^α-Boc protected aspartic acid with allyl bromide in the presence of lithium bis(trimethylsilyl)amide (LHMDS) and hexamethylphosphoramide (HMPA) afforded chiral β-allyl substituted aspartic acid in good yields. After deprotection of the N^α-Boc group and reprotection as a trifluoroacetamide, the terminal alkene was oxidized to an aldehyde. The aldehyde was then coupled with L-cysteine through a cascade three-bond formation process to afford aspartic acid-glycine bicyclic dipeptide mimetics.

Original language	English (US)
Pages (from-to)	3245-3247
Number of pages	3
Journal	Tetrahedron Letters
Volume	45
Issue number	16
DOIs	https://doi.org/10.1016/j.tetlet.2004.02.117
State	Published - Apr 12 2004
Externally published	Yes

Keywords

Bicyclic dipeptide
Cholecystokinin
Trifluoroacetamide
β-substituted aspartic acid

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2004.02.117

Cite this

@article{74e6a8a0f19b42d5ab9a5429eecbdbc8,

title = "A simple and efficient synthesis of an Asp-Gly dipeptide mimetic",

abstract = "Alkylation of Nα-Boc protected aspartic acid with allyl bromide in the presence of lithium bis(trimethylsilyl)amide (LHMDS) and hexamethylphosphoramide (HMPA) afforded chiral β-allyl substituted aspartic acid in good yields. After deprotection of the Nα-Boc group and reprotection as a trifluoroacetamide, the terminal alkene was oxidized to an aldehyde. The aldehyde was then coupled with L-cysteine through a cascade three-bond formation process to afford aspartic acid-glycine bicyclic dipeptide mimetics.",

keywords = "Bicyclic dipeptide, Cholecystokinin, Trifluoroacetamide, β-substituted aspartic acid",

author = "Ndungu, {John M.} and Xuyuan Gu and Gross, {Dustin E.} and Jinfa Ying and Hruby, {Victor J.}",

note = "Funding Information: This work was supported by US Public Health Service (DA 06284 and DA 13449). NMR was acquired using a DRX 500 MHz spectrometer obtained by a grant from the NSF(9729350). The views expressed in this article are those of the authors and are not necessarily those of the USPHS.",

year = "2004",

month = apr,

day = "12",

doi = "10.1016/j.tetlet.2004.02.117",

language = "English (US)",

volume = "45",

pages = "3245--3247",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "16",

}

TY - JOUR

T1 - A simple and efficient synthesis of an Asp-Gly dipeptide mimetic

AU - Ndungu, John M.

AU - Gu, Xuyuan

AU - Gross, Dustin E.

AU - Ying, Jinfa

AU - Hruby, Victor J.

N1 - Funding Information: This work was supported by US Public Health Service (DA 06284 and DA 13449). NMR was acquired using a DRX 500 MHz spectrometer obtained by a grant from the NSF(9729350). The views expressed in this article are those of the authors and are not necessarily those of the USPHS.

PY - 2004/4/12

Y1 - 2004/4/12

N2 - Alkylation of Nα-Boc protected aspartic acid with allyl bromide in the presence of lithium bis(trimethylsilyl)amide (LHMDS) and hexamethylphosphoramide (HMPA) afforded chiral β-allyl substituted aspartic acid in good yields. After deprotection of the Nα-Boc group and reprotection as a trifluoroacetamide, the terminal alkene was oxidized to an aldehyde. The aldehyde was then coupled with L-cysteine through a cascade three-bond formation process to afford aspartic acid-glycine bicyclic dipeptide mimetics.

AB - Alkylation of Nα-Boc protected aspartic acid with allyl bromide in the presence of lithium bis(trimethylsilyl)amide (LHMDS) and hexamethylphosphoramide (HMPA) afforded chiral β-allyl substituted aspartic acid in good yields. After deprotection of the Nα-Boc group and reprotection as a trifluoroacetamide, the terminal alkene was oxidized to an aldehyde. The aldehyde was then coupled with L-cysteine through a cascade three-bond formation process to afford aspartic acid-glycine bicyclic dipeptide mimetics.

KW - Bicyclic dipeptide

KW - Cholecystokinin

KW - Trifluoroacetamide

KW - β-substituted aspartic acid

UR - http://www.scopus.com/inward/record.url?scp=1642634979&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=1642634979&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2004.02.117

DO - 10.1016/j.tetlet.2004.02.117

M3 - Article

AN - SCOPUS:1642634979

SN - 0040-4039

VL - 45

SP - 3245

EP - 3247

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 16

ER -

A simple and efficient synthesis of an Asp-Gly dipeptide mimetic

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this