Home
Resources
Publications
1-N-acylation of Gentamicin C1a by a Cyclic, Chiral Gamma-Amino-Alpha-Hydroxy Acid Related to the (S)-4-amino-2-hydroxybutyric Acid

1-N-acylation of Gentamicin C1a by a Cyclic, Chiral Gamma-Amino-Alpha-Hydroxy Acid Related to the (S)-4-amino-2-hydroxybutyric Acid

M Philippe, A M Sepulchre, S D Gero, H Loibner, W Streicher, P Stutz

J Antibiot (Tokyo). 1982 Nov;35(11):1507-12.

PMID: 7161190

Abstract:

A semisynthetic aminoglycoside antibiotic 15, containing a cyclic gamma-amino-alpha-hydroxy acid, related to the 1-N-4-amino-2-hydroxybutyric acid (AHBA) side chain of butirosins and amikacin, has been prepared. Conveniently protected 3,2',6'-tris-N-tert-butoxycarbonylgentamicin C1a (12) was condensed with the phtalimido active ester 10 to give after catalytic reduction and deprotection, the hitherto unknown 1-N-substituted gentamicin C1a 15. The requisite side chain was synthesized from the readily available D-(-)-quinic acid. The antibacterial properties of 15 are given.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP3347908	(S)-2-Hydroxybutyric acid		3347-90-8	Price

As a specialist in analytical chemical Products, Alfa Chemistry offers consumers a wealth of raw materials and a full range of technologies and services.

QUICK LINKS

HEADQUARTERS

Tel:

Fax:

Email: