Abstract
Peracetylated N-acetylneuraminic acid (NeuAc) was efficiently coupled to esters of glycine, alanine, and serine using BOP and HOBT in the presence of DIEA. Deprotection of the esters readied the NeuAc-α-amino acid conjugates for further elaboration. Coupling of the NeuAc-gly adduct with β-O-methoxy neuraminic acid methyl ester afforded a selectively protected glycine linked sialic acid dimer. 2-Amino-3,4-di-O-benzyl-(1→6)-anhydroglucose and alanine benzyl ester were also efficiently coupled to the bis adduct giving novel trimeric analogs. Elimination of the anomeric acetate from the NeuAc-gly dimer followed by global deprotection provided a novel saccharopeptide with modest clostridial sialidase inhibitory activity.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 7801-7805 |
| Number of pages | 5 |
| Journal | Journal of Organic Chemistry |
| Volume | 62 |
| Issue number | 22 |
| State | Published - 1997 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
Solution Phase Synthesis of Amide-Linked N-Acetyl Neuraminic Acid, α-Amino Acid, and Sugar Amino Acid Conjugates. / Ramamoorthy, P. S.; Gervay-Hague, Jacquelyn.
In: Journal of Organic Chemistry, Vol. 62, No. 22, 1997, p. 7801-7805.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Solution Phase Synthesis of Amide-Linked N-Acetyl Neuraminic Acid, α-Amino Acid, and Sugar Amino Acid Conjugates
AU - Ramamoorthy, P. S.
AU - Gervay-Hague, Jacquelyn
PY - 1997
Y1 - 1997
N2 - Peracetylated N-acetylneuraminic acid (NeuAc) was efficiently coupled to esters of glycine, alanine, and serine using BOP and HOBT in the presence of DIEA. Deprotection of the esters readied the NeuAc-α-amino acid conjugates for further elaboration. Coupling of the NeuAc-gly adduct with β-O-methoxy neuraminic acid methyl ester afforded a selectively protected glycine linked sialic acid dimer. 2-Amino-3,4-di-O-benzyl-(1→6)-anhydroglucose and alanine benzyl ester were also efficiently coupled to the bis adduct giving novel trimeric analogs. Elimination of the anomeric acetate from the NeuAc-gly dimer followed by global deprotection provided a novel saccharopeptide with modest clostridial sialidase inhibitory activity.
AB - Peracetylated N-acetylneuraminic acid (NeuAc) was efficiently coupled to esters of glycine, alanine, and serine using BOP and HOBT in the presence of DIEA. Deprotection of the esters readied the NeuAc-α-amino acid conjugates for further elaboration. Coupling of the NeuAc-gly adduct with β-O-methoxy neuraminic acid methyl ester afforded a selectively protected glycine linked sialic acid dimer. 2-Amino-3,4-di-O-benzyl-(1→6)-anhydroglucose and alanine benzyl ester were also efficiently coupled to the bis adduct giving novel trimeric analogs. Elimination of the anomeric acetate from the NeuAc-gly dimer followed by global deprotection provided a novel saccharopeptide with modest clostridial sialidase inhibitory activity.
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UR - http://www.scopus.com/inward/citedby.url?scp=0001231422&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:0001231422
VL - 62
SP - 7801
EP - 7805
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 22
ER -