Synthesis and structural analysis of a β-hairpin peptide containing a sugar amino acid

B. Aguilera; G. Siegal; H.S. Overkleeft; N.J. Meeuwenoord; F.P.J.T. Rutjes; J.C.M. Hest, van; H.E. Schoemaker; G.A. van der Marel; J.H. van Boom; M. Overhand

Synthesis and structural analysis of a β-hairpin peptide containing a sugar amino acid

B. Aguilera
, G. Siegal
, H.S. Overkleeft
, N.J. Meeuwenoord
, F.P.J.T. Rutjes
, J.C.M. Hest, van
, H.E. Schoemaker
, G.A. van der Marel
, J.H. van Boom
, M. Overhand

Onderzoeksoutput: Bijdrage aan tijdschrift › Tijdschriftartikel › Academic › peer review

Samenvatting

The solid-phase synthesis of the linear peptide II (Ac-KKYTVSI-SAA2-KKITVSI) containing the novel sugar amino acid SAA2 [(2S,3S,6R)-6-aminomethyl-3-hydroxytetrahydro-pyran-2-carboxylic acid] is described. Structural analysis by NMR and CD in 50% aqueous methanol indicates that peptide II adopts a β-hairpin conformation, as reported earlier for the non-modified peptide I (Ac-KKYTVSINGKKITVSI).

Originele taal-2	Engels
Pagina's (van-tot)	1541-1547
Aantal pagina's	7
Tijdschrift	European Journal of Organic Chemistry
Nummer van het tijdschrift	8
Status	Gepubliceerd - 2001
Extern gepubliceerd	Ja

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@article{4e50dbaaea2949f384c9575044a1c290,

title = "Synthesis and structural analysis of a β-hairpin peptide containing a sugar amino acid",

abstract = "The solid-phase synthesis of the linear peptide II (Ac-KKYTVSI-SAA2-KKITVSI) containing the novel sugar amino acid SAA2 [(2S,3S,6R)-6-aminomethyl-3-hydroxytetrahydro-pyran-2-carboxylic acid] is described. Structural analysis by NMR and CD in 50\% aqueous methanol indicates that peptide II adopts a β-hairpin conformation, as reported earlier for the non-modified peptide I (Ac-KKYTVSINGKKITVSI).",

keywords = "β-Hairpin, β-Turn, Peptide isosters, Peptides, Sugar amino acids",

author = "B. Aguilera and G. Siegal and H.S. Overkleeft and N.J. Meeuwenoord and F.P.J.T. Rutjes and \{Hest, van\}, J.C.M. and H.E. Schoemaker and \{van der Marel\}, G.A. and \{van Boom\}, J.H. and M. Overhand",

year = "2001",

language = "English",

pages = "1541--1547",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

number = "8",

}

TY - JOUR

T1 - Synthesis and structural analysis of a β-hairpin peptide containing a sugar amino acid

AU - Aguilera, B.

AU - Siegal, G.

AU - Overkleeft, H.S.

AU - Meeuwenoord, N.J.

AU - Rutjes, F.P.J.T.

AU - Hest, van, J.C.M.

AU - Schoemaker, H.E.

AU - van der Marel, G.A.

AU - van Boom, J.H.

AU - Overhand, M.

PY - 2001

Y1 - 2001

N2 - The solid-phase synthesis of the linear peptide II (Ac-KKYTVSI-SAA2-KKITVSI) containing the novel sugar amino acid SAA2 [(2S,3S,6R)-6-aminomethyl-3-hydroxytetrahydro-pyran-2-carboxylic acid] is described. Structural analysis by NMR and CD in 50% aqueous methanol indicates that peptide II adopts a β-hairpin conformation, as reported earlier for the non-modified peptide I (Ac-KKYTVSINGKKITVSI).

AB - The solid-phase synthesis of the linear peptide II (Ac-KKYTVSI-SAA2-KKITVSI) containing the novel sugar amino acid SAA2 [(2S,3S,6R)-6-aminomethyl-3-hydroxytetrahydro-pyran-2-carboxylic acid] is described. Structural analysis by NMR and CD in 50% aqueous methanol indicates that peptide II adopts a β-hairpin conformation, as reported earlier for the non-modified peptide I (Ac-KKYTVSINGKKITVSI).

KW - β-Hairpin

KW - β-Turn

KW - Peptide isosters

KW - Peptides

KW - Sugar amino acids

UR - https://www.scopus.com/pages/publications/0035044727

M3 - Article

AN - SCOPUS:0035044727

SN - 1434-193X

SP - 1541

EP - 1547

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 8

ER -

Synthesis and structural analysis of a β-hairpin peptide containing a sugar amino acid

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